Ionic liquids: A class of versatile green reaction media for the syntheses of nitrogen heterocycles

Current Organic Synthesis

Volumn 8, Issue 3, 2011, Pages 438-471

  Chaturvedi, Devdutt ^a  

^a CSIR NORTH EAST INSTITUTE OF SCIENCE AND TECHNOLOGY   (India)

Author keywords

Ionic liquids; Nitrogen heterocycles

Indexed keywords

EID: 79955739158     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017911795529092     Document Type: Article

References (248)

1. Wasserchied, P.; Keim, W. Ionic liquids: New solutions for transition metal catalysis. Angew. Chem. Int. Ed., 2000, 39, 3772-3789.
2. Larshen, fA. S.; Holbrey, J. D.; Than, F. S.; Reed, C. A. Designing ionic liquids: Imidazolium melts with inert carbonate anions. J. Am. Chem. Soc., 2000, 122, 7264-7272.
3. Balaban, A. T.; Oniciu, D. C.; Katritzky, A. R. Aromaticity as a cornerstone of heterocyclic chemistry. Chem. Rev., 2004, 104, 2777-2812.
4. Martins, M. A. P.; Frizzo, C. P.; Moreira, D. N.; Zanatta, N.; Bonacorso, H. G. Ionic liquids in heterocyclic synthesis. Chem. Rev., 2008, 108, 2015-2050.
5. Chowdhury, S.; Mohan, R. S.; Scott, J. L. Reactivity of ionic liquids. Tetrahedron, 2007, 63, 2363-2389;
6. Parvulescu, V. I.; Hardacre, C. Catalysis in ionic liquids. Chem. Rev., 2007, 107, 2615-2665.
7. Greaves, T. L.; Drummond, C. J. Protic ionic liquids: Properties and applica-tions. Chem. Rev., 2008, 108, 206-237.
8. Ibuka, T. The aza-Payne rearrangement: A synthetically valuable equilibra-tion. Chem. Soc. Rev., 1998, 27, 145-154.
9. Murphree, S. S.; Padwa, A. Three-membered ring systems. Prog. Heterocycl. Chem., 2001, 13, 52-70.
10. Sun, W.; Xia, C. G.; Wang, H. W. Synthesis of aziridines from imines and ethyl diazoacetate in room temperature ionic liquids. Tetrahedron Lett., 2003, 44, 2409-2411.
11. Xie, W. H.; Fang, J. W.; Li, J.; Wang, P. G. Aziridine synthesis in protic media by using lanthanide triflates as catalysts. Tetrahedron, 1999, 55, 12929-12938.
12. Xue, Z.; Mazumdar, A.; Hope-Weeks, L. J.; Mayer, M. F. Aziridine synthesis in the presence of catalytic amounts of pyridiniums or viologens. Tetra-hedron Lett., 2008, 49, 4601-4603.
13. Zoidis, G.; Fytas, C.; Papanastasiou, L.; Foscolos, G. B.; Fytas, G.; Padalko, E.; Clereq, E. D.; Naesens, L.; Neyts, J.; Kolocouris, N. Heterocyclic rimantadine analogues with antiviral activity. Bioorg. Med. Chem., 2006, 14, 3341-3348.
14. Nishiyama, S.; Kikuchi, Y.; Kurata, H.; Yamamura, S.; Izawa, T.; Nagahata, T.; Ikeda, R.; Kato, K. Enantiomerically pure synthesis and antiviral evaluation of [(2 S, 3 S)-bis(hydroxymethyl)azetidin-1-yl] purine nucleosides: Ana-logs of oxetanocin-A. Bioorg. Med. Chem. Lett., 1995, 5, 2273-2276.
15. Yadav, V. K.; Sriramurthy, V. Silylmethyl-substituted aziridine and azetidine as masked 1,3 and 1,4-dipoles for formal [3 + 2] and [4 + 2] cycloaddition reactions. J. Am. Chem. Soc., 2005, 127, 16366-16367.
16. Cromwell, N. H.; Phillips, B. The azetidines: Recent synthetic developments. Chem. Rev., 1979, 79, 331-358.
17. Yadav, L. D. S.; Patel, R.; Srivastava, V. P. Chalcones to functionalized azetidines via anion induced cyclization using task specific ionic liquids. Synlett, 2008, 583-585.
18. Jacobi, P. A.; Coults, L. D.; Guo, J. S.; Leung, S. I. New strategies for the synthesis of biologically important tetrapyrroles: The "B,C + D + A" approach to linear tetrapyrroles. J. Org. Chem., 2000, 65, 205-213.
19. March, J. Advanced organic chemistry. 4th ed, 1999, John Wiley & Sons publishers Ltd.
20. Roomi, M. W.; McDonald, S. F. The Hantzsch pyrrole synthesis. Can. J. Chem., 1970, 48, 1689-1697.
21. Katritzky, A. R.; Yao, J.; Bao, W.; Qi, M.; Steel, P. J. 2-Benzotriazolylaziridines and their reactions with diethyl acetylenedicarboxylate. J. Org. Chem., 1999, 64, 346-350.
22. Minetto, G.; Raveglia, L. F.; Taddei, M. Microwave-assisted Paal Knorr reaction: A rapid approach to substituted pyrroles and furans. Org. Lett., 2004, 6, 389-392.
23. Wang, B.; Gu, Y.; Luo, C.; Yang, T.; Yang, L.; Suo, J. Pyrrole synthesis in ionic liquids by Paal-Knoor condensation under mild conditions. Tetrahedron Lett., 2004, 45, 3417-3419.
24. Yadav, J. S.; Reddy, B. V. S.; Eeshwaraiah, B.; Gupta, M. K. Bi(OTf)3/[bmim]BF4 as novel and reusable catalytic system for the synthesis of furan, pyrrole and thiophene derivatives. Tetrahedron Lett., 2004, 45,5873-5876.
25. Yavari, I.; Kowsari, E. Task-specific basic ionic liquids: A reusable and green catalyst for one-pot synthesis of highly functionalized pyrroles in aqueous media. Synlett, 2008, 897-899.
26. Lednicer, D.; Mitscher, L. A. Organic Chemistry of Drugs Synthesis A: Wiley: New York, 1977, Vol. 1-3.
27. Katrizky, A. R.; Rees, C. W.; Scriven, E. F. V. Comprehensive Heterocyclic Chemistry II: Elsevier Science: New York, 1996, Vol 3.
28. Bonacorso, H. G.; Oliveira, M. R.; Wentz, A. P.; Wastowski, A. D.; Oliveri-ra, A. B.; Hoener, M.; Zanatta, N.; Martins, M. A. P. Haloacetylated enol ethers: 12 [18]: Regiospecific synthesis and structural determination of stable 5-hydroxy-1H-pyrazolines. Tetrahedron, 1999, 55, 345-352.
29. Moreira, D. N.; Frizzo, C. P.; Longhi, K.; Zanatta, N.; Bonacorso, H. G.; Martins, M. A. P. An efficient synthesis of 1-cyanoacetyl-5-halomethyl-4,5- dihydro-1H-pyrazoles in ionic liquid. Monatsh. Chem., 2008, 139, 1049-1054.
30. Ghahremanzadeh, R.; Shakibaei, G. I.; Bazgir, A. An efficient, one-pot synthesis of 1H-pyrazolo [1,2-b] phthalazine-5,10-dione derivatives. Synlett, 2008, 1129-1132.
31. Lambardino, J. G.; Wiseman, E. H. Preparation and anti-inflammatory activ-ity of some nonacidic trisubstituted imidazoles. J. Med. Chem., 1974, 17, 1182-1188.
32. Lantos, I.; Zhang, W. Y.; Shiu, X.; Eggleston, D. S. Synthesis of imidazoles via hetero-Cope rearrangements. J. Org. Chem., 1993, 58, 7092-7095.
33. Zhang, C.; Moran, E. J.; Woiwade, T. F.; Short, K. M.; Mjalli, A. M. M. Synthesis of tetrasubstituted imidazoles via -(N-acyl-N-alkylamino)- -ketoamides on wang resin Tetrahedron Lett., 1996, 37, 751-754.
34. Claiborne, C. F.; Liverton, N. J.; Nguyen, K. T. An efficient synthesis oftetrasubstituted imidazoles from N-(2-oxo)-amides. Tetrahedron Lett., 1998,39, 8939-8942.
35. Bleicher, K. H.; Gerber, F.; Wuthrich, Y.; Alanine, A.; Capretta, A. Parallelsynthesis of substituted imidazoles from 1,2-aminoalcohols. TetrahedronLett., 2002, 43, 7687-7690.
36. Liu, J.; Chen, J.; Zhao, J.; Zhao, Y.; Li, L.; Zhang, H. A modified procedurefor the synthesis of 1-arylimidazoles. Synthesis, 2003, 2661-2666.
37. Sarsar, S.; Seiv, D.; Mjalli, A. M. M. Imidazole libraries on solid support.Tetrahedron Lett., 1996, 37, 835-838.
38. Frantz, D. E., Morency, L.; Soheili, A.; Murray, J. A.; Grabowski, E. J. J.;Tillyer, R. D. Synthesis of substituted imidazoles via organocatalysis. Org.Lett., 2004, 6, 843-838.
39. Weinmann, H.; Harre, M.; Koeing, K.; Merten, E.; Tilstam, U. Efficient andenvironmentally friendly synthesis of 2-amino-imidazole. Tetrahedron Lett.,2002, 43, 593-595.
40. Xie, Y. Y.; Chen, Z. C.; Zheng, Q. G. Organic reactions in ionic liquids:Ionic liquid-accelerated cyclocondensation of -tosyloxyketones with 2-aminopyridine. Synthesis, 2002, 1505-1508.
41. Xu, D. Q.; Liu, B. Y.; Xu, Z. Y. Synthesis of 2-arylimidazo [1,2-a]pyrimidines in ionic liquids. Chin. Chem. Lett., 2003, 14, 1002-1004.
42. Nadaf, R. N.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, K.V. Room temperature ionic liquid promoted regioselective synthesis of 2-arylbenzimidazoles, benzooxazoles, and benzotriazoles under ambient condi-tions. J. Mol. Catal. A Chem., 2004, 214, 155-160.
43. Xie, Y. Y. Organic reactions in ionic liquids: Ionic liquid accelerated one-potsynthesis of 2-arylimidazo [1,2-a] pyrimidines. Synth. Commun., 2005, 35,1741-1746.
44. Siddiqui, S. A.; Narkhede, U. C.; Palimkar, S. S.; Daniel, T.; Lahoti, R.J.; Srinivasan, K. V. Room temperature ionic liquid promoted improved andrapid synthesis of 2,4,5-triaryl imidazoles from aryl aldehydes and 1,2-diketones or -hydroxyketone. Tetrahedron, 2005, 61, 3539-3546.
45. Shaabani, A.; Soleimani, E.; Maleki, A. Ionic liquid promoted one-pot syn-thesis of 3-aminoimidazo [1,2-a] pyridines. Tetrahedron Lett., 2006, 47,3031-3034.
46. Shaabani, A.; Rahmati, A.; Aghaaliakbari, B.; Safaei-Ghomi, J. 1,1,3,3-N,N,N',N'-Tetramethylguanidinium trifluoroacetate ionic liquid-promotedefficient one-pot synthesis of trisubstituted imidazoles. Synth. Commun.,2006, 36, 65-70.
47. Shaabani, A.; Maleki, A. Ionic liquid promoted one-pot three-componentreaction: Synthesis of annulated imidazo [1,2-a] azines using trimethylsilyl-cyanide. Monatsh. Chem., 2007, 138, 51-56.
48. Ma, H.; Wang, Y.; Li, J.; Wang, J. Selective synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles promoted by ionic liquid. Heterocycles,2007, 71, 135-140.
49. Xia, M.; Lu, Y. D. A novel neutral ionic liquid-catalyzed solvent free synthe-sis of 2,4,5-trisubstituted imidazoles under microwave irradiation. J. Mol.Catal. A Chem., 2007, 265, 205-208.
50. Khodaei, M. M.; Bahrami, K.; Kavianinia, I. p-TSA Catalyzed synthesis of2,4,5-triarylimidazoles from ammonium heptamolybdate tetrahydrate inTBAI. J. Chin. Chem. Soc., 2007, 54, 829-833.
51. Shaabani, A.; Rahmati, A.; Farhangi, E.; Rezayan, A. H. One-step synthesisof 3,4-dihydrobenimidazo [2,1-b] quinazoline-1(2H)-ones in an ionic liquid.Monatsh. Chem., 2007, 138, 615-618.
52. Labbe, G. Decomposition and addition reactions of organic azides. Chem.Rev., 1969, 69, 345-363.
53. Gothelf, K. V.; Jorgensen, K. A. Asymmetric 1,3-dipolar cycloadditionreactions. Chem. Rev., 1998, 98, 863-910.
54. Rostovtsev, V. V.; Green, G. L.; Fokin, V. V.; Sharpless, K. B. A stepwiseHuisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation"of azides and terminal alkynes. Angew. Chem. Int. Ed., 2002, 41, 2596-2599.
55. Zhao, Y. B.; Yan, Z. Y.; Liang, Y. M. Efficient synthesis of 1,4-disubstituted1,2,3-triazoles in ionic liquid/water system. Tetrahedron Lett., 2006, 47,1545-1549.
56. Butler, R. N. Comprehensive Organic Chemistry; Katrizky, AR, Rees CW,Scriven EF, Eds.; Pergamon: Oxford, UK, 1996, Vol. 4.
57. Singh, H.; Chawla, A. S.; Kapoor, V. K.; Paul, D.; Malhotra, R. K. Medicinalchemistry of tetrazoles. Prog. Med. Chem., 1980, 17, 151-183.
58. Ostrovskii, V. A.; Pevzner, M. S.; Kofmna, T. P.; Shcherbinin, M.B.; Tselinskii, I. V. Energetic 1,2,4-triazoles and tetrazoles synthesis, structureand properties. Targets Heterocycl. Syst., 1999, 3, 467-526.
59. Burger, A. Isosterism and bioisosterism in drug design. Prog. Drug Res.,1991, 37, 287-371.
60. Fallon, F. G.; Herbst, R. M. Synthesis of 1-substituted tetrazoles. J. Org.Chem., 1957, 22, 933-936.
61. Jin, T.; Kamijo, S.; Yamamoto, Y. Synthesis of 1-substituted tetrazoles viathe acid-catalyzed [3+2] cycloaddition between isocyanides and trimethyl-silyl azide. Tetrahedron Lett., 2004, 45, 9435-9437.
62. Gupta, A. K.; Oh, C. H. 1-(2-Iodophenyl)-1H-tetrazole as a ligand for Pd(II)catalyzed Heck reaction. Tetrahedron Lett., 2004, 45, 4113-4116.
63. Su, W.; Hong, Z.; Shan, W.; Zhang, X. A. Facile synthesis of 1-substituted-1H-1,2,3,4-tetrazoles catalyzed by ytterbium triflate hydrate. Eur. J. Org.Chem., 2006, 2723-2726.
64. Schmidt, B.; Meid, D.; Kieser, D. Safe and fast tetrazole formation in ionicliquid 1-n-butylimidazolium tetrafluoroborae. Tetrahedron, 2007, 63, 492-496.
65. Potewar, T. M.; Siddiqui, S. A.; Lahoti, R. J.; Srinivasan, K.V. Efficient andrapid synthesis of 1-substituted-1H-1,2,3,4-tetrazoles in the acidic ionic liq-uids Tetrahedron Lett., 2007, 48, 1721-1724.
66. Robinson, B. Studies on the Fischer indole synthesis. Chem Rev., 1969, 69,227-250.
67. Humphrey, G. R.; Kuethe, J. T. Practical methodologies for the synthesis ofindoles. Chem. Rev., 2006, 106, 2875-2911.
68. Robinson, G. M.; Robinson, R. Mechanism of E. Fischer's synthesis ofindoles. Application of the method to the preparation of a pyrindole deriva-tive. J. Chem. Soc. Trans., 1924, 827-840.
69. Hiller, M. C.; Marcoux, J. F.; Zhao, D.; Grabowski, E. J. J.; Mckeon, A.E.; Tillyer, R. D. Stereoselective formation of carbon-carbon bonds via SN2-displacement: Synthesis of substituted cycloalkyl[b]indoles. J. Org. Chem.,2005, 70, 8385-8394.
70. Ackermann, L.; Born, R. TiCl4/t-BuNH2 as the sole catalyst for a hydroami-nation-based Fischer indole synthesis. Tetrahedron Lett., 2004, 45, 9541-9544.
71. Mhaske, S. B.; Argade, N. P. Facile zeolite induced Fischer-indole synthesis:A new approach to bioactive natural product rutaecarpine. Tetrahedron,2004, 60, 3417-3420.
72. Morales, R. C.; Tambyrajah, V.; Jenkins, P. R.; Davies, D. L.; Abbott, A. P.The regiospecific Fischer indole reaction in choline chloride.2ZnCl2 withproduct isolation by direct sublimation from the ionic liquid. Chem. Com-mun., 2004, 158-159.
73. Xu, D. Q.; Yang, W. L.; Luo, S. P.; Wang, B. T.; Wu, J.; Xu, Z.Y. Fischer indole synthesis in Bronsted acidic ionic liquids: A green, mild, andregiospecific reaction system. Eur. J. Org. Chem., 2007, 1007-1012.
74. Ma, X.; Gang, D. R. The Lycopodium alkaloids. Nat. Prod. Rep., 2004, 21,752-772.
75. Fletcher, M. D.; Hurst, T. E.; Miles, T. J.; Moody, C. J. Synthesis of highly-functionalized pyridines via hetero-Diels-Alder methodology: reaction of 3-siloxy-1-aza-1,3-butadienes with electron deficient acetylenes. Tetrahedron,2006, 62, 5454-5463.
76. Evdokimov, N. M.; Magedov, I. V.; Kireev, A. S.; Kornienko, A. One-step,three-component synthesis of pyridines and 1,4-dihydropyridines with mani-fold medicinal utility. Org. Lett., 2006, 8, 899-902.
77. Mavassaghi, M.; Hill, M. D. Synthesis of substituted pyridine derivatives viathe Ruthenium-catalyzed cycloisomerization of 3-Azadienynes. J. Am.Chem. Soc., 2006, 128, 4592-4593.
78. Winter, A.; Risch, N. Cross Mannich reaction of aldehydes: Efficient synthe-sis of substituted pyridines. Synthesis, 2003, 2667-2670.
79. Thomas, A. D.; Ashokan, C. V. Vilsmeier-Haack reactions of -hydroxyketenedithioacetals: A facile synthesis of substituted pyridines. Tet-rahedron Lett., 2002, 43, 2273-2275.
80. Tanaka, K.; Mori, H.; Yamamoto, M.; Katsumara, S. Significant accelerationof 6 -azaelectrocyclization resulting from a remarkable substituent effect andformal synthesis of the ocular age pigment A2-E by a new method for substi-tuted pyridine synthesis. J. Org. Chem., 2001, 66, 3099-3110.
81. Mashraqui, S. H.; Karnik, M. A. Catalytic oxidation of Hantzsch 1,4-dihydropyridines by RuCl3 under oxygen atmosphere. Tetrahedron Lett.,1998, 39, 4895-4898.
82. Singh, K.; Singh, J.; Singh, H. Carbon transfer reactions of functionalizedoxazolidines and their open chain enamine tautomers to enamine nucleo-philes. A facile synthesis of substituted pyridines and ring annulated deriva-tives. Tetrahedron, 1998, 54, 935-942.
83. Renslo, A. R.; Danheiser, R. L. Synthesis of substituted pyridines via regio-controlled [4 + 2] cycloadditions of oximinosulfonates. J. Org. Chem.,1998, 63, 7840-7850.
84. Ahmed, S.; Boruah, R. C. An efficient conversion of conjugated oximes intosubstituted pyridines under Vilsmeier conditions. Tetrahedron Lett., 1996,37, 8231-8232.
85. Komatsu, M.; Ohgishi, H.; Takamatsu, S.; Ohshiro, Y.; Agawa, T. A newroute to pyridine derivatives: Reaction of N-methylene-tert-butylamine withenamine. Angew. Chem. Int. Ed. Engl., 1982, 21, 213-214.
86. Van Aken, K. J.; Lux, G. M.; Deroover, G. G.; Meerpoel, L.; Hoornaert, G.J. The Synthesis of 3-functionalized 5-chloro-6-methyl-2H-1,4-oxazin-2-ones and of pyridines from cycloaddition-elimination reactions with substi-tuted acetylenic compounds. Tetrahedron, 1994, 50, 5211-5224.
87. Anabha, E. R.; Nirmala, K. N.; Thomas, A.; Asokan, C. V. Synthesis of 3-aroylnicotinonitriles from aroylketene dithioacetals. Synthesis, 2007, 428-432.
88. Zhong, P.; Hu, H.; Guo, S. Direct formation of 2,3,5-trichloropyridine and itsnucleophilic displacement reactions in ionic liquid. Synth. Commun., 2004,34, 4301-4311.
89. Karthikeyan, G.; Perumal, P. T. Ionic liquid-promoted simple and efficientsynthesis of -enamino esters and -enaminones from 1,3-dicarbonyl com-pounds: One-pot, three-component reaction for the synthesis of substitutedpyridines. Can. J. Chem., 2005, 83, 1746-1751.
90. Ranu, B. C.; Jana, R.; Sowmiah, S. An improved procedure for the three-component synthesis of highly substituted pyridines using ionic liquid. J.Org. Chem., 2007, 72, 3152-3154.
91. Zhang, X. Y.; Li, X. Y.; Fan, X. S.; Wang, X.; Wang, J. J.; Qu, G. R. Anovel synthesis of pyrazolo [3,4-b] pyridine derivatives through multi-component reaction in ionic liquid. Chin. Chem. Lett., 2008, 19, 153-156.
92. Wang, X. S.; Wu, J. R.; Li, Q.; Yao, C. S.; Tu, S. J. A novel and greenmethod for the synthesis of indeno [2,1-c]pyridine derivatives in ionic liquidcatalyzed by malononitrile. Synlett., 2008, 1185-1188.
93. Stout, D. M.; Meyers, A. I. Recent advances in the chemistry of dihydropyri-dines. Chem. Rev., 1982, 82, 223-243.
94. Bossert, F.; Vater, W. 1,4-Dihydropyridines - A basis for developing newdrugs. Med. Res. Rev., 1989, 9, 291-324.
95. Hantzsch, A. Ueber die synthese pyridinartiger verbindungen aus acetes-sigäther und aldehydammoniak. Liebigs. Ann. Chem., 1882, 215, 1-82.
96. Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Narsaiah, A. V. Three-component coupling reactions in ionic liquids: An improved protocol for thesynthesis of 1,4-dihydropyridines. Green Chem., 2003, 5, 60-63.
97. Sridhar, R.; Perumal, P. T. A new protocol to synthesize 1,4-dihydropyridines by using 3,4,5-trifluorobenzeneboronic acid as a catalyst inionic liquid: Synthesis of novel 4-(3-carboxyl-1H-pyrazol-4-yl)-1,4-dihydropyridines. Tetrahedron, 2005, 61, 2465-2470.
98. Shaabani, A.; Rezayan, A. H.; Rahmati, A.; Sharifi, M. Ultrasound acceler-ated synthesis of 1,4-dihydropyridines in an ionic liquid. Monatsh. Chem.,2006, 137, 77-81.
99. Zhang, X. Y.; Li, Y. Z.; Fan, X. S.; Qu, G. R.; Hu, X. Y.; Wang, J. J. Mul-ticomponent reaction in ionic liquid: a novel and green synthesis of 1, 4-di-hydropyridine derivatives. Chin. Chem. Lett., 2006, 17, 150-152.
100. Waldmann, H. Asymmetric hetero Diels-Alder reactions. Synthesis, 1994,535-551.
101. Hattori, K.; Yamamoto, H. Asymmetric aza-Diels-Alder reaction catalyzedby boron reagent: Effect of biphenol and binaphthol ligand. Synlett., 1993,129-130.
102. Kervin, J. F. J.; Danishefsky, S. On the lewis acid catalyzed cyclocondensa-tion of imines with a siloxydiene. Tetrahedron Lett., 1982, 23, 3739-3742.
103. Kobayashi, S.; Araki, M.; Inshitani, H.; Nagayama, S.; Hachiya, I. Activationof imines by rare earth metal triflates. Ln(OTf)3 or Sc(OTf)3-catalyzed reac-tions of imines with silyl enolates and Diels-Alder reactions of imines. Syn-lett, 1995, 233-234.
104. Akiyama, T.; Takaya, J.; Kagoshima, H. Brønsted acid-catalyzed aza Diels-Alder reaction of Danishefsky's diene with aldimine generated in situ fromaldehyde and amine in aqueous media. Tetrahedron Lett., 1999, 40, 7831-7834.
105. Zulfiqar, F.; Kitazume, T. One-pot aza-Diels-Alder reactions in ionic liquids.Green Chem., 2000, 2, 137-139.
106. Pegot, B.; Vo-Thanh, G. Ionic liquid promoted aza-Diels-Alder reaction ofDanishefsky's diene with imines. Synlett., 2005, 1409-1412.
107. Pigot, B.; Buu, O. V.; Gori, D.; Vo-Than, G. Asymmetric aza-Diels- Alderreaction of Danishefsky's diene with imines in a chiral reaction medium. Beilstein J. Org. Chem., 2006, 2, 1-6.
108. Jurkik, V.; Wilhelm, R. The preparation of new enantiopure imidazoliniumsalts and their evaluation as catalysts and shift reagents. Tetrahedron Asym-metry, 2006, 17, 801-810.
109. Ojima, I.; Delaloge, F. Asymmetric synthesis of building-blocks for peptidesand peptidomimetics by means of the -lactam synthon method. Chem. Soc.Rev., 1997, 26, 377-386.
110. Singh, G. S. β -Lactams in the new millennium. Part-I: Monobactams andcarbapenems. Mini Rev. Med. Chem., 2004, 4, 69-92.
111. Banik, F.; Beker, F.; Banik, B. K. Stereoselective synthesis of -lactams withpolyaromatic imines: Entry to new and novel anticancer agents. J. Med.Chem., 2003, 46, 12-15.
112. Zhou, N. E.; Guo, D.; Thomas, G.; Reddy, A. V. N.; Kaleta, J.; Purisima, E.; Menard, R.; Micetich, R. G.; Singh, R. 3-Acylamino-azetidin-2-one as anovel class of cysteine proteases inhibitors. Bioorg. Med. Chem. Lett., 2003,13, 139-141.
113. Calet, S.; Urso, F.; Alper, H. Enantiospecific and stereospecific rhodium (I)-catalyzed carbonylation and ring expansion of aziridines: Asymmetric syn-thesis of.beta.-lactams and the kinetic resolution of aziridines. J. Am. Chem.Soc., 1989, 111, 931-934.
114. Ananda, M.; Hashimoto, S. I. Enantioselective intramolecular C-H insertionroute to a key intermediate for the synthesis of trinem antibiotics. Tetrahe-dron Lett., 1998, 39, 9063-9066.
115. Lo, M. M. C.; Fu, G. C. Cu(I)/bis(azaferrocene)-catalyzed enantioselectivesynthesis of -lactams via couplings of alkynes with nitrones J. Am. Chem.Soc., 2002, 124, 4572-4573.
116. Fijida, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. A ternary complexreagent for an asymmetric reaction of lithium ester enolates with imines. J.Am. Chem. Soc., 1997, 119, 2060-2061.
117. Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J.; Lectka, T. Catalytic, asymmetric synthesis of -lactams. J. Am. Chem. Soc., 2000, 122,7831-7832.
118. Peng, J.; Deng, Y. Catalytic Beckmann rearrangement of ketoximes in ionicliquids. Tetrahedron Lett., 2001, 42, 403-405.
119. Ren, R. X.; Zueva, L. Z.; Qu, W. Formation of -caprolactam via catalyticBeckmann rearrangement using P2O5 in ionic liquids. Tetrahedron Lett.,2001, 42, 8441-8443.
120. Qiao, K.; Deng, Y.; Yokoyama, C.; Sato, H.; Yamasina, M. Preparation of -caprolactam via Beckmann rearrangement of cyclohexanone oxime: A mildand recyclable process. Chem. Lett., 2004, 33, 1350-1351.
121. Kamimura, A.; Yamamoto, S. An efficient method to depolymerize polyam-ide plastics: A new use of ionic liquids. Org. Lett., 2007, 9, 2533-2535.
122. Gois, P. M. P., Afonso, C. A. M. Dirhodium (II)-catalyzed C-H insertion on-diazo--phosphono-acetamides in an ionic liquid. Tetrahedron Lett., 2003,44, 6571-6573.
123. Chen, R.; Yang, B.; Su, W. Ytterbium (III) triflate catalyzed stereoselectivesynthesis of -lactams via [2+2] cyclocondensation in ionic liquid. Synth.Commun., 2006, 36, 3167-3174.
124. Tao, X. L.; Lei, M.; Wang, Y. G. Ionic liquid supported synthesis of -lactam library in ionic liquids batch. Tetrahedron Lett., 2007, 48, 5143-5146.
125. Feroci, M.; Chiarotto, I.; Orsini, M.; Sotqiu, G.; Inesi, I. Reactivity of elec-trogenerated N-heterocyclic carbenes in room-temperature ionic liquids: Cy-clization to 2-azetidinone ring via C-3/C-4 bond formation. Adv. Synth.Catal., 2008, 350, 1355-1359.
126. Orrling, K. M.; Wu, X.; Russo, F.; Larhed, M. Fast, acid free and selectivelactamization of lactones in ionic liquids. J. Org. Chem., 2008, 73, 8627-8630.
127. Chauhan, P. M. S.; Srivastava, S. K. Present trends and future strategy inchemotherapy of malaria. Curr. Med. Chem., 2001, 8, 1535-1542.
128. Lu, L.; Jenekhe, S. A. Poly(vinyl diphenylquinoline): A new pH-tunablelight-emitting and charge-transport polymer synthesized by a simplemodification of polystyrene. Macromolecules, 2001, 34, 6249-6254.
129. Cho, C. S.; Oh, B. H.; Kim, T. J.; Shim, S. C. Synthesis of quinolines viaruthenium-catalysed amine exchange reaction between anilines and trialky-lamines. Chem. Commun., 2000, 1885-1886.
130. Hoemann, M. Z.; Kumaravel, G.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Potent in vitro methicillin-resistant Staphylo-coccus aureus activity of 2-(1H-indol-3-yl)quinoline derivatives. Bioorg.Med. Chem. Lett., 2000, 10, 2675-2678.
131. Du, W.; Curran, D. P. Synthesis of carbocyclic and heterocyclic fused quino-lines by cascade radical annulations of unsaturated N-aryl thiocarbamates,thioamides, and thioureas. Org. Lett., 2003, 5, 1765-1768.
132. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Manas, M. M.; Vallribera, A. The[(E, E, E)-1,6,11-tris(p-toluenesulfonyl)-1,6,11-triazacyclopentadeca-3,8,13-triene] Pd(0) complex in the hydroarylation of alkynes in ionic liquids: Anapproach to quinolines. Tetrahedron Lett., 2002, 43, 5537-5540.
133. Palimkar, S. S.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. Ionic liquid promoted regiospecific Friedlander annulation: Novel synthesisof quinolines and fused polycyclic quinolines. J. Org. Chem., 2003, 68,9371-9378.
134. Karthikeyan, G.; Perumal, P. T. A mild efficient and improved protocol forthe Friedlander synthesis of quinolines using Lewis acidic ionic liquid J.Heterocycl. Chem. 2004, 41, 1039-1041.
135. Zhang, X. Y.; Fan, X. S.; Wang, J. J.; Li, Y. Z. A novel green synthesis ofquinolines through acid catalyzed Friedlander reaction in ionic liquids. Chin.Chem. Lett., 2004, 15, 1170-1172.
136. Wang, J. J.; Fan, X. S.; Zhang, X. Y.; Han, L. J. Green preparation of quino-line derivatives through FeCl3.6H2O-catalyzed Friedlander reaction in ionicliquids. Can. J. Chem., 2004, 82, 1192-1196.
137. Zhang, X. Y.; Fan, X. S.; Wang, J. J.; Li, Y. Z. A novel preparation of 4-phenylquinoline derivatives in ionic liquids. J. Chin. Chem. Soc., 2004, 51,1339-1342.
138. Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Nikcheh, M. S. A new and effi-cient one-pot procedure for the synthesis of 2-styrylquinolines. TetrahedronLett., 2008, 49, 5366-5368.
139. Sharma, R.; Prajapati, D. Ionic liquid: An efficient recyclable system for thesynthesis of 2,4-disubstituted quinolines via Meyer-Schuster rearrangement. Synlett., 2008, 3001-3005.
140. Li, Y.; Wu, C.; Huang, J.; Su, W. Mild and convenient synthesis of 1,2-dihydroquinolines from anilines and acetone catalyzed by ytter-bium(III)triflate in ionic liquids. Synth. Commun., 2006, 36, 3065-3073.
141. Ye, F.; Alper, H. Ionic liquid promoted palladium catalyzed multicomponentcyclocarbonylation of o-iodoanilines and allenes to form methylene-2,3-dihydro-1H-quinolin-4-ones. J. Org. Chem., 2007, 72, 3218-3222.
142. Ma, C.; Ren, Y.; Zhang, Q.; Ding, K.; Zhao, J.; Zhang, D. A novel one-potsynthesis of pyrroloquinolines and pyrroloisoquinolines derivatives in ionicliquids. Chem. Lett., 2007, 36, 1152-1153.
143. Wang, X. Z.; Zhang, M. M.; Jiang, H.; Yao, C. S.; Tu, S. J. Three componentgreen synthesis of N-arylquinoline derivatives in ionic liquid [Bmim]BF4:Reactions of aryl aldehyde, 3-arylamino-5,5-dimethyl cyclo-hex-2-enone andactive methylene compounds. Tetrahedron, 2007, 63, 4439-4449.
144. Shamma, M. The Isoquinoline Alkaliods: Chemistry and Pharmacology; Academic Press: New York, 1972.
145. Gerhard, B.; Matthias, W.; Ross, K. T.; Michael, R. B.; Robert, J. G.; Ronald, K. Octadehydromichellamine, a structural analog of the anti-HIVmichellamines without centrochirality. Tetrahedron, 1999, 55, 1731-1740.
146. Czerwinski, K. M.; Cook, J. M. Stereochemical control of the Pictet-Spengler reaction in the synthesis of natural products. Adv. Heterocyl. Nat.Prod. Synth., 1996, 3, 217-277.
147. Sotomayer, N.; Dominguez, E.; Lete, E. Bischler-Napieralski cycliza-tion N/C-alkylation sequences for the construction of isoquinoline alkaloids:Synthesis of protoberberines and benzo[c]phenanthridines via C-2'-functionalized 3-arylisoquinolines. J. Org. Chem., 1996, 61, 4062-4072.
148. Judeh, Z. M. A.; Ching, C. B.; Bu, J.; McCluskey, A. The first Bischer-Napieralski cyclization in a room temperature ionic liquid. Tetrahedron Lett.,2002, 43, 5089-5091.
149. Wang, H. M.; Hou, R. S.; Huang, H. Y.; Chen, L. C. Ionic liquid in organicsynthesis: The Pictet-Spengler reaction. Heterocycles, 2006, 68, 1651-1658.
150. Yadav, J. S.; Reddy, B. V. S.; Raj, K. S.; Prasad, A. R. Room temperatureionic liquids promoted three-component coupling reactions: A facile synthe-sis of cis-isoquinolinic acids. Tetrahedron, 2003, 59, 1805-1809.
151. Hassine, H.; Gmouh, S.; Pucheault, M.; Vaultier, M. Task specific oniumsalts and ionic liquids as soluble supports in Grieco's multicomponent syn-thesis of tetrahydroquinolines. Monatsh. Chem., 2007, 138, 1167-1174.
152. Couture, E. D.; Grandclaudon, P.; Hoarau, C. Total syntheses of taliscanine,velutinam, and enterocarpam II. J. Org. Chem., 1998, 63, 3128-3132.
153. Charles, D. H.; Aristotle, G. P. Preparation of acyclic imides. J. Org. Chem.,1959, 24, 388-392.
154. Aubert, M. T.; Farnier, M.; Guilard, R. Reactivity of iminophosphoranestowards some symmetrical dicarbonyl dichlorides: Syntheses and mecha-nisms. Tetrahedron, 1991, 47, 53-60.
155. Zhou, M. Y.; Li, Y. Q.; Xu, X. M. A new simple and efficient synthesis of N-aryl phthalimides in ionic liquid [Bmim]PF6. Synth. Commun., 2003, 33,3777-3780.
156. Le, Z. G.; Chen, Z. C.; Hu, Y.; Zheng, Q. G. Organic reactions in ionicliquids: Ionic liquid promoted efficient synthesis of N-alkyl and N-arylphthalimides. J. Heterocylic Chem., 2005, 42, 735-737.
157. Chen, D. C.; Ye, H. Q.; Wu, H. Ionic liquid [Bmim]BF4 acts as solvent andpromoter for synthesis of halo containing N-arylphthalimides. Chin. Chem.Lett., 2007, 18, 27-29.
158. Chen, D. C.; Ye, H. Q.; Wu, H. A more efficient synthetic process of N-arylphthalimides in ionic liquid [Bmim]BF4. Catal. Commun., 2007, 8, 1527-1530.
159. Eisner, U.; Kuthan, J. Chemistry of dihydropyridines. Chem. Rev., 1972, 72,1-42.
160. Martin, N.; Quinteiro, M.; Seoane, C.; Mora, L.; Suraez, M.; Ockoa, E.; Morales, A. Synthesis and conformational study of acridine derivatives re-lated to 1,4-dihydropyridines. J. Heterocyclic Chem., 1995, 51, 235-238.
161. Wang, X. S.; Shi, D. Q.; Zhang, Y. F.; Wang, S. H.; Tu, S. J. Synthesis of 9-arylpolyhydroacridine in water catalyzed by triethylbenzylammonium chlo-ride (TEBA). Chin. J. Org. Chem., 2004, 24, 430-432.
162. Tu, S. J.; Miao, C. B.; Gao, Y.; Feng, F. J.; Feng, J. C. Synthesis of substi-tuted acridines under microwave irradiation. Chin. J. Chem., 2002, 20, 703-706.
163. Li, Y. L.; Zhang, M. M.; Wang, X. S.; Shi, D. Q.; Tu, S. J.; Wei, X. Y.; Zong, Z. M. Efficient synthesis of substituted aroyl polyacridines under mi-crowave irradiation. J. Chem. Res., 2005, 600-604.
164. Yadav, J. S.; Reddy, B. V. S.; Chetia, L.; Srinivasulu, G.; Kunwar, A. C. Ionic liquid accelerated intramolecular hetero-Diels-Alder reactions: A pro-tocol for the synthesis of octahydroacridines. Tetrahedron Lett., 2005, 46,1039-1044.
165. Lenardão, E. J.; Mendes, S. R.; Ferreira, P. C.; Perin, G.; Silveira, C. C.; Jacob, R. G. Selenium and tellurium-based ionic liquids and their use in thesynthesis of octahydroacridines. Tetrahedron Lett., 2006, 47, 7439-7442.
166. Wang, X. S.; Zhang, M. M.; Jiang, H.; Shi, D. Q.; Tu, S. J.; Wei, X. Y.; Zonh, Z. M. An improved and benign synthesis of 9,10-diarylacridine-1,8-dione and indenoquinoline derivatives from 3-anilino-5,5-dimethylyclohex-2-enones, benzaldehydes and 1,3-dicarbonyl compounds in an ionic liquidmedium. Synthesis, 2006, 4187-4199.
167. Dabiri, M.; Baghbanzaheh, M.; Arzroomchilar, E. 1-Methylimidazoliumtrifluoroacetate ([Hmim] TFA): An efficient reusable acidic ionic liquid forthe synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacri-dines. Catal. Commun., 2008, 9, 939-942.
168. Kappe, C. O. Recent advances in the Biginelli dihydropyrimidine synthesis.New tricks from an old dog. Acc. Chem. Res., 2000, 33, 879-888.
169. Aron, Z. D.; Overman, L. E. The tethered Biginelli condensation in naturalproduct synthesis. Chem. Commun., 2004, 253-265.
170. Biginelli, P. Aldureides of ethylic acetoacetate and ethylic oxalacetate. Gazz.Chim. Ital., 1893, 23, 360-416.
171. Dondoni, A.; Massi, A. Design and synthesis of new classes of heterocyclicC-glycoconjugates and carbon-linked sugar and heterocyclic amino acids byasymmetric multicomponent reactions (AMCRs). Acc. Chem. Res., 2006, 39,451-463.
172. Peng, J.; Deng, Y. Ionic liquids catalyzed Biginelli reaction under solventfree conditions. Tetrahedron Lett., 2001, 42, 5917-5919.
173. Golap, A. R.; Venketsan, K.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. Ionicliquid promoted novel and efficient one pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones at ambient temperature under ultrasound irra-diation. Green Chem., 2004, 6, 147-150.
174. Shaabani, A.; Rahmati, A. Ionic liquid promoted efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-ones. Catal. Lett., 2005, 100, 177-179.
175. Khosropour, A. R.; Khodae, M. M.; Beygzadel, M.; Jokar, M. A one-potsynthesis of 3,4-dihydropyrimidin-2-(1H)-ones from primary alcohols pro-moted by Bi(NO3)2.5H2O in two different media: Organic solvent and ionicliquid. Heterocycles, 2005, 65, 767-773.
176. Wang, Z. T.; Wang, S. C.; Xu, L. W. Polymer supported ionic liquid cata-lyzed synthesis of 1,2,3,4-tetrahydro-2-oxopyrimine-5-carboxylates via Bigi-nelli reaction. Helv. Chim. Acta., 2005, 88, 986-989.
177. Zheng, R.; Wang, X.; Xu, H.; Du, J. Brønsted acidic ionic liquid: An effi-cient and reusable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Synth. Commun., 2006, 36, 1503-1513.
178. Li, M.; Guo, W. S.; Wen, L. R.; Li, Y. F.; Yang, H. Z. One-pot synthesis ofBiginelli and Hantzsch products catalyzed by non-toxic ionic liquid[Bmim]Sac and structural determination of two products. J. Mol. Catal. A:Chem. 2006, 258, 133-138.
179. Jain, S. L.; Joseph, J. K.; Sain, B. Ionic liquid promoted an improved synthe-sis of 3,4-dihyropyrimidinones using [Bmim]BF4 immobilized Cu (II) acety-lacetone as recyclable catalytic system. Catal. Lett., 2007, 115, 52-55.
180. Arfan, A.; Paquin, L.; Bajureau, J. P. Task specific ionic liquid as catalyst ofmicrowave assisted solvent free Biginelli reaction. Russ. J. Org. Chem.,2007, 43, 1058-1064.
181. Dong, F.; Jun, L.; Xinli, Z.; Zhiwen, Y.; Zuliang, L. One-pot green procedurefor Biginelli reaction catalyzed by novel task-specific room temperatureionic liquids. J. Mol. Catal. A Chem., 2007, 274, 208-211.
182. Yadav, L. D. S.; Rai, A.; Rai, V. K.; Awasthi, C. Chiral ionic liquid-catalyzed Biginelli reaction: Stereoselective synthesis of polyfunctionalizedperhydropyrimidines. Tetrahedron, 2008, 64, 1420-1429.
183. Hakkou, H.; Eynde, J. J. V.; Hamelin, J.; Bazureau, J. P. Ionic liquid phaseorganic synthesis methodology applied to the three component preparation of2-thioxo tetrahydropyrimidin-4-(1H)-ones under microwave dielectric heat-ing. Tetrahedron, 2004, 60, 3745-3753.
184. Legeay, J. C.; Eynde, J. J. V.; Hamelin, J.; Bazureau, J. P. Ionic liquid phasetechnology supported the three component synthesis of Hantzsch 1,4-dihydropyridines and Biginelli 3,4-dihydropyrimidin-2(1H)-ones under mi-crowave dielectric heating. Tetrahedron, 2005, 61, 12386-12397.
185. Legeay, J. C.; Eynde, J. J. V.; Toupet, L.; Bazureau, J. P. A three-componentcondensation protocol based on ionic liquid phase bound acetoacetate for thesynthesis of Biginelli-3,4-dihydropyrimidine-2(1H)-ones. Arkivoc, 2007, 3,13-28.
186. Legeay, J. C.; Eynde, J. J. V.; Bazureau, J. P. Ionic liquid phase organicsynthesis methodology applied to the preparation of new 3,4-dihydropyrimidin-2(1H)-ones bearing bioisostere group in N-3 position. Tet-rahedron, 2008, 64, 5328-5335.
187. Michael, J. P. Quinoline, quinazoline and acridone alkaloids. Nat. Prod.Rep., 2003, 20, 476-493.
188. Kung, P. P.; Casper, M. D.; Cook, K. L.; Wilson-Lingardo, L.; Risen, L. M.; Vickers, T. A.; Ranken, R.; Blyn, L. B.; Wyatt, J. R.; Cook, P. D.; Ecker, D.J. J. Med. Chem., 1999, 42, 4705.
189. Baek, D. J.; Park, Y. K.; Heo, H. I.; Lee, M.; Yang, Z.; Choi, M. Synthesis of5-substituted quinazolinone derivatives and their inhibitory activity in vitro.Bioorg. Med. Chem. Lett., 1998, 8, 3287-3290.
190. Kikuchi, H.; Tasaka, H.; Hirai, S.; Takaya, Y.; Iwabuchi, Y.; Ooi, H.; Hata-keyama, S.; Kim, H. S.; Wataya, Y.; Oshima, Y. Potent antimalarial febrifug-ine analogues against the Plasmodium malaria parasite. J. Med. Chem., 2002,45, 2563-2570.
191. Chao, Q.; Deng, L.; Shih, H.; Leoni, L. M.; Genini, D.; Carson, D. A.; Cot-tam, H. B. Substituted isoquinolines and quinazolines as potential antiin-flammatory agents. Synthesis and biological evaluation of inhibitors of tumornecrosis factor. J. Med. Chem., 1999, 42, 3860-3873.
192. Malamas, M. S.; Millen, J. Quinazolineacetic acids and related analogs asaldose reductase inhibitors. J. Med. Chem., 1991, 34, 1492-1503.
193. Mannschreck, A.; Koller, H.; Stuehler, G.; Davies, M. A.; Traber, J. Theenantiomers of methaqualone and their unequal anticonvulsive activity. Eur.J. Med. Chem., 1984, 19, 381-383.
194. Katritzky, A. R. Comprehensive Heterocyclic Chemistry: The Structure,Reaction, Synthesis and uses of Heterocyclic Compounds; Rees CW Ed, Per-gamon: Oxford, 1984, Vol. 3, Part 2B.
195. Kuehl, F. A.; Spencer, C. F.; Folkers, K. Alkaloids of dichroa febrifuga lour.J. Am. Chem. Soc., 1948, 70, 2091-2093.
196. Wang, H.; Genesan, A. Total Synthesis of the quinazoline alkaloids ()-Fumiquinazoline G and ()-Fiscalin B. J. Org. Chem., 1998, 63, 2432-2433.
197. Kornet, M. J.; Varia, T.; Beaven, W. Synthesis of 3-amino-2,4(1H,3H)-quinazolinediones for testing as anticonvulsants. J. Heterocycl. Chem., 1984,21, 1533-1535.
198. Tayler, E. C.; Shvo, Y. Heterocyclic synthesis from o-aminonitriles. XXX.Synthesis of some diazasteroids. J. Org. Chem., 1968, 33, 1719-1727.
199. Peter, R. 2-Aryl-4(3H) quinazolinones.J. Heterocycl. Chem., 1971, 8, 699-702.
200. Takeuchi, H.; Hagiwara, S.; Eguchi, S. A new efficient synthesis of imida-zolinones and quinazolinone by intramolecular aza-Wittig reaction. Tetrahe-dron, 1989, 45, 6375-6386.
201. Paterson, M. T.; Smalle, R. K.; Suschitzky, H. 1,2,3-Benzotriazin-4-ones andrelated systems. part III. Thermal decomposition of 3-arylideneamino-1,2,3-benzotriazin-4-ones. A new synthesis of 2-arylquinazolin-4-ones. Synthesis,1975, 187-188.
202. Das, R.; Vig, O. P.; Gupta, I. S.; Narang, K. S. Antimalarials, I. Quinazolineseries. J. Sci. Ind. Res., 1952, 11B 461-463.
203. Imai, Y.; Sato, S.; Takasawa, R.; Umeda, M. Facile syntheses of 2H-1,2,4-benzothiadiazine 1,1-dioxides and 4-oxo-3,4-dihydroquinazolines from 2-aminobenzenesulfonamide or 2-aminobenzamide and aldehydes in the pres-ence of sodium hydrogen sulfite. Synthesis, 1981, 35-36.
204. Yang, R. Y.; Kaplan, A. A concise and efficient solid-phase synthesis of 2-amino-4(3H)-quinazolinones. Tetrahedron Lett., 2000, 41, 7005-7008.
205. Wang, L.; Xia, J.; Quin, F.; Quian, C.; Sun, J. Yb(OTf)3-Catalyzed one-potsynthesis of quinazolin-4(3H)-ones from anthranilic acid, amines and orthoesters (or formic Acid) in solvent-free conditions. Synthesis, 2003, 1241-1247.
206. Hazarkhani, H.; Karimi, B. A facile synthesis of new 3-(2-benzimidazolyl)-2-alkyl-4-(3H)-quinazolinones under microwave irradiation. Tetrahedron,2003, 59, 4757-4760.
207. Akazome, M.; Kondo, T.; Watanabe, Y. Transition-metal complex-catalyzedreductive N-heterocyclization: synthesis of 4(3H)-quinazolinone derivativesfrom N-(2-nitrobenzoyl)amides. J. Org. Chem., 1993, 58, 310-312.
208. Kundu, N. G.; Chaudhari, G. Copper-catalysed heteroannulation with al-kynes: A general and highly regio- and stereoselective method for the syn-thesis of (E)-2-(2-arylvinyl) quinazolinones. Tetrahedron, 2001, 57, 6833-6842.
209. Potewar, T. M.; Nadaf, R. N.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. Anovel one-pot synthesis of 2-aryl-4(3H)-quinazolinones using room tempera-ture ionic liquid as reaction medium as well as promotor. Synth. Commun.,2005, 35, 231-241.
210. Khosropour, A. R.; Baltork, I. M.; Ghorbankhani, H. Bi(TFA)3-[nbp]FeCl4:A new, efficient and reusable promotor system for the synthesis of 4(3H)-quinazolinone derivatives. Tetrahedron Lett., 2006, 47, 3561-3564.
211. Chen, J. S.; Su, W.; Wu, H.; Liu, M.; Jin, C. Eco-friendly synthesis of 2,3-dihydro-quinazolin-4(1H)-ones in ionic liquids or ionic liquid-water withoutadditional catalyst. Green Chem., 2007, 9, 972-975.
212. Dabiri, M.; Salehi. P.; Baghbanzadeh, M. Ionic liquid promoted eco-friendlyand efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones. Monatsh.Chem., 2007, 138, 1191-1194.
213. Portela-Cubillo, F.; Scott, J. S.; Walton, J. C. 2-(aminoaryl)alkanone O-phenyl oximes: Versatile reagents for the syntheses of quinazolines. Chem.Commun., 2008, 2935-2937.
214. Srinivasan, N.; Ganesan, A. Highly efficient Lewis acid-catalysed Pictet-Spengler reactions discovered by parallel screening. Chem. Commun., 2003,916-917.
215. Cox, E. D.; Cook, J. M. The Pictet-Spengler condensation: a new directionfor an old reaction. Chem. Rev., 1995, 95, 1797-1842.
216. Cui, C. B.; Kakeya, H.; Okada, G.; Onose, R.; Osada, H. Novel mammaliancell cycle inhibitors, tryprostatins A, B and other diketopiperazines producedby Aspergillus fumigatus. I. Taxonomy, fermentation, isolation and biologi-cal properties. J. Antibiot., 1996, 49, 527-533.
217. Chicharro, R.; de Castro, S.; Reino, J. L.; Aran, V. J. Synthesis of tri-andtetracyclic condensed quinoxalin-2-ones fused across the C-3-N-4 bond. Eur.J. Org. Chem., 2003, 2314-2326.
218. Wang, H.; Ganesan, A. The N-Acyliminium Pictet-Spengler condensation asa multicomponent combinatorial reaction on solid phase and its applicationto the synthesis of demethoxyfumitremorgin C analogues. Org. Lett., 1999,1, 1647-1649.
219. Willardsen, J. A.; Dedley, D. A.; Cody, W. L.; Chi, L.; McClanahan, T. B.; Mertz, T. E.; Potoczak, R. E.; Narasimhan, L. S.; Holland, D. R.; Rapundalo, S. T.; Edmunds, J. J. Design, synthesis, and biological activity of potent andselective inhibitors of blood coagulation factor Xa. J. Med. Chem., 2004, 47,4089-4099.
220. Joshi, R. A.; Muthukrishnan, M.; More, S. V.; Garud, D. R.; Ramana, C. V.; Joshi, R. R. Pictet-spengler cyclization in room temperature ionic liquid: Aconvenient access to tetrahydro- -carbolines. J. Heterocycl. Chem., 2006, 43,767-772.
221. Yen, Y. H.; Chu, Y. H. Synthesis of tetrahydro- -carbolinediketopiperazinesin [Bdmim]PF6 ionic liquid accelerated by controlled microwave heating.Tetrahedron Lett., 2004, 45, 8137-8140.
222. Tseng, M. C.; Liang, Y. M.; Chu, Y. H. Synthesis of fused tetrahydro- -carboline --quinoxalinones in 1-n-butyl-2, 3-dimethylimidazolium bis(trifluoromethylsulfonyl)-imide ([Bdmim]Tf2N) and 1-n-butyl-2,3-dimethylimidazolium perfluorobutylsulfonate ([Bdmim]PFBuSO3) ionic liq-uids. Tetrahedron Lett., 2005, 46, 6131-6136.
223. Smolin, E. M.; Rapoport, L. s-Triazines and Derivatives; Interscience; NewYork, 1959, Chapter IV, p. 217.
224. Parker, B.; Son, D. Y. Silylated amino-triazines: new ligands with potentialmulti-coordination modes. Inorg. Chem. Commun., 2002, 5, 516-518.
225. Ogino, A.; Matsumara, S.; Fujita, T. Structure-activity study of antiulcerousand antiinflammatory drugs by discriminant analysis. J. Med. Chem., 1980,23, 437-444.
226. Deans, R.; Cook, G.; Rotello, V. M. Model systems for flavoenzyme activity.Regulation of flavin recognition via modulation of receptor hydrogen-bonddonor-acceptor properties. J. Org. Chem., 1997, 62, 836-839.
227. Smyrl, N. R.; Smithwick, R. W. Hydroxide-catalyzed synthesis of heterocyc-lic aromatic amine derivatives from nitriles. J. Heterocycl. Chem., 1982, 19,493-496.
228. Peng, Y.; Song, G. Microwave-assisted clean synthesis of 6-aryl-2,4-diamino-1,3,5-triazines in [Bmim]PF6. Tetrahedron Lett., 2004, 45, 5313-5316.
229. Potewar, T. M.; Lahoti, R. J.; Daniel, T.; Srinivasan, K. V. Efficient synthe-sis of 3,5,6-trisubstituted 1,2,4-triazines in the Bronsted acidic ionic liquid,1-n-butylimidazoium tetrafluoroborate. Synth. Commun., 2007, 37, 261-269.
230. Schutz, H. Benzodiazepines; Springer Verlag: Heidelberg, Germany, 1982.
231. Landquist, J. K. Comprehensive Heterocyclic Chemistry; Katritzky, A. R;Rees, C. W. (Eds); Pergamon: Oxford, 1984, Vol. 1, 116.
232. Essaber, M.; Baouid, A.; Hasnaoui, A; Benharreb, A.; Lavergne, J. P. Synthesis of new tri- and tetraheterocyclic systems: 1,3-Dipolar cycloaddi-tion of nitrilimines on 2,7-dimethyl-4-Phenyl-3H-1,5-benzodiazepine. Synth.Commun., 1998, 28, 4097-4104.
233. El-Sayed, A. M.; Abdel-Ghany, H.; El-Saghier, A. M. M. A novel synthesisof pyrano(2,3-c)-1,3-oxazino(2,3 b)-1,2,4-triazolo(3,4-b)-oxazolo(2,3-b)-furano (3,2-c) and 3-substituted-(1,5) benzodiazepin-2-ones. Synth. Com-mun., 1999, 29, 3561-3572.
234. Zhang, X. Y.; Xu, J. X.; Jin, S. Synthesis of oxadiazolobenzodiazepines. Chin. J. Chem., 1999, 17, 404-408.
235. Reddy, K. V. V.; Rao, P. S.; Ashok, D. A facile synthesis of 2-benzoyl-6-hydroxy-3-methyl-5-(2-substituted-2,3-dihydro-1H-1,5-benzodiazepin-4-YL)benzo[b]furans. Synth. Commun., 2000, 30, 1825-1836.
236. Herbert, J. A. L.; Suschitzky, H. The chemistry of pseudomonic acid. Part12. Preparation of diazole and triazole derivatives. J. Chem. Soc. PerkinTrans. I, 1994, 2657-2666.
237. Morales, H. R.; Bulbarela, A.; Contreras, R. New synthesis of dihydro-andtetrahydro-1,5-benzodiazepines by reductive condensation of o-phenylenediamine and ketones in the presence of sodium borohydride. Het-erocycles, 1986, 24, 135-139.
238. Jung, D. I.; Choi, T. W.; Kim, Y. Y.; Kim, I. S.; Park, Y. M.; Lee, Y. G.; Jung, D. H. Synthesis of 1,5-benzodiazepine derivatives. Synth. Commun.,1999, 29, 1941-1951.
239. Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Ytterbium triflatepromoted synthesis of 1,5-benzodiazepine derivatives. Tetrahedron Lett.,2001, 42, 3193-3195.
240. Balakrishna, M. S.; Kaboudin, B. A simple and new method for the synthesisof 1,5-benzodiazepine derivatives on a solid surface. Tetrahedron Lett.,2001, 42, 1127-1129.
241. Pozarentzi, M.; Stephanidou, S. J.; Tsoleridis, C. A. An efficient method forthe synthesis of 1,5-benzodiazepine derivatives under microwave irradiationwithout solvent. Tetrahedron Lett., 2002, 43, 1755-1758.
242. Ma, Y.; Zhang, Y. Derivatives of 2,3-dihydro-1H-1,5-benzodiazepine fromo-nitroanilines and chalcones induced by low valent titanium. Synth Com-mun., 2002, 32, 165-169.
243. Reddy, B. M.; Srikanth, P. M. An efficient synthesis of 1,5-benzodiazepinederivatives catalyzed by a solid superacid sulfated zirconia. TetrahedronLett., 2003, 44, 4447-4449.
244. Kodomari, M.; Naguchi, T.; Aoyama, T. Solvent-free synthesis of 1,5-benzothiazepines and benzodiazepines on inorganic supports. Synth Com-mun., 2004, 34, 1783-1790.
245. Sabitha, G.; Reddy, G. S. K. K.; Reddy, K. B.; Reddy, N. M.; Yadav, J. S. Anew, efficient and environmentally benign protocol for the synthesis of 1,5-benzodiazepines using cerium(III) chloride/sodium iodide supported on silicagel. Adv. Synth. Catal., 2004, 346, 921-924.
246. Yadav, J. S.; Reddy, B. V. S.; Eshwaraiah, B.; Anuradha, K. Amberlyst-15:A novel and recyclable reagent for the synthesis of 1,5-benzodiazepines inionic liquids. Green Chem., 2002, 4, 592-594.
247. Jarikote, D. V.; Siddiqui, S. A.; Rajagopal, R.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. Room temperature ionic liquid promoted synthesis of 1,5-benzodiazepine derivatives under ambient conditions. Tetrahedron Lett.,2003, 44, 1835-1838.
248. 4 acidic ionic liquid as a novel,efficient, and environmentally benign catalyst for the synthesis of 1,5-benzodiazepines under mild conditions. Synth. Commun., 2006, 36, 1661-1669.