Efficient and eco-friendly synthesis of dihydropyrimidinones, bis(indolyl)methanes, and N-alkyl and N-arylimides in ionic liquids

Journal of the Iranian Chemical Society

Volumn 4, Issue 4, 2007, Pages 393-401

  Dabiri, M ^a   Salehi, P ^a   Baghbanzadeh, M ^a   Shakouri, M ^a   Otokesh, S ^a   Ekrami, T ^a   Doosti, R ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

Bis(indolyl)methanes; Dihydropyrimidinones; Green chemistry; Ionic liquid; N substituted cyclic imides

Indexed keywords

EID: 36549010105     PISSN: 1735207X     EISSN: 17352428     Source Type: Journal    
DOI: 10.1007/BF03247224     Document Type: Article

References (87)

1. a) G.C. Rovnyak, S.D. Kimball, B. Beyer, G. Cucinotta, J.D. DiMarco, J. Gougoutas, A. Hedberg, M. Mally, J.P. McCarthy, R. Zhang, S. Moreland, J. Med. Chem. 38 (1995) 119;
2. b) K.S. Atwal, G.C. Rovnyak, S.D. Kimball, D.M. Floyd, S. Moreland, B.N. Swanson, J.Z. Gougoutas, J. Schwartz, K.M. Smillie, M.F. Malley, J. Med. Chem. 33 (1990) 2629;
3. c) G.C. Rovnyak, K.S. Atwal, A. Hedberg, S.D. Kimball, S. Moreland, J.Z. Gougoutas, B.S. O'Reilly, J. Schawartz, M.F. Malley, J. Med. Chem. 35 (1992) 3254;
4. e) C.O. Kappe, Eur. J. Med. Chem. 35 (2000) 1043.
5. a) A.D. Patil, N.V. Kumar, W.C. Kokke, M.F. Bean, A.J. Freyer, C. De Brosse, S. Mai, A. Truneh, D.J. Faulkner, B. Carte, A.L. Breen, R.P. Hertzberg, R.K. Johnson, J.W. Westley, B.C. Potts, J. Org. Chem. 60 (1995) 1182;
6. b) B.B. Snider, J. Chen, A.D. Patil, A. Freyer, Tetrahedron Lett. 37 (1996) 6977.
7. P. Biginelli, Gazz. Chim. Ital. 23 (1893) 360.
8. a) A.K. Bose, M.S. Manhas, S. Pednekar, S.N. Ganguly, H. Dang, W. He, A. Mandadi, Tetrahedron Lett. 46 (2005) 1901;
9. b) J. Azizian, A.A. Mohammadi, A.R. Karimi, M.R. Mohammadizadeh, Appl. Catal. A Gen. 300 (2006) 85.
10. a) S.K. De, R.A. Gibbs, Synthesis (2005) 1748;
11. b) R. Ghosh, S. Maiti, A. Chakraborty, J. Mol. Catal. A Chem. 217 (2004) 47;
12. c) Z.T. Wang, L.W. Xu, C.G. Xia, H.Q. Wang, Tetrahedron Lett. 45 (2004) 7951;
13. d) W. Su, J. Li, Z. Zheng, Y. Shen, Tetrahedron Lett. 46 (2005) 6037;
14. e) S. Balalaie, M. Soleiman-Beigi, F. Rominger, J. Iran. Chem. Soc. 2 (2005) 319;
15. f) G. Sabitha, K.B. Reddy, J.S. Yadav, D. Shailaja, K.S. Sivudu, Tetrahedron Lett. 46 (2005) 8221.
16. a) V.R. Choudhary, V.H. Tillu, V.S. NarkHede, H.B. Borate, R.D. Wakharkar, Catal. Commun. 40 (2000) 449;
17. b) S. Martinz, M. Meseguer, L. Casas, E. Rodriguez, E. Molins, M.M. Manas, A. Roig, R.M. Sebastian, A. Villibera, Tetrahedron 59 (2003) 1553.
18. a) A. Shaabani, A. Bazgir, F. Teimouri, Tetrahedron Lett. 44 (2003) 857;
19. b) K.R. Reddy, C.V. Reddy, M. Mahesh, P.V.K. Raju, N. Reddy, Tetrahedron Lett. 44 (2003) 8173.
20. a) G. Maiti, P. Kundu, C. Guin, Tetrahedron Lett. 44 (2003) 2757;
21. b) P.P. Baruah, S. Gadhwal, D. Prajapati, J.S. Sandhu, Chem. Lett. (2002) 1038.
22. J.S. Yadav, B.V.S. Reddy, K.B. Reddy, K.S. Raj, A. Prasad, J. Chem. Soc. Perkin Trans. 1 (2001) 1939.
23. a) J. Peng, Y. Deng, Tetrahedron Lett. 42 (2001) 5917;
24. b) A.R. Gholap, K. Venkatesan, T. Daniel, R.J. Lahoti, K.V. Srinivasan, Green Chem. 6 (2004) 147.
25. R.J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1970.
26. a) M.A. Zeligs, J. Med. Food 1 (1998) 67;
27. b) M.J. Anderton, M.M. Manson, R. Verschoyle, A. Gescher, W.P. Steward, M.L. Williams, D.E. Mager, Drug Metab. Dispos. 32 (2004) 632;
28. c) C. Bonnesen, I.M. Eggleston, J.D. Hayes, Cancer Res. 61 (2001) 6120;
29. d) Y.C. Cang, J. Riby, G.H. Chang, B. Peng, G. Firestone, L.F. Bjeldanes, Biochem. Pharmacol. 58 (1999) 825;
30. e) H.T. Le, C.M. Schaldach, G. Firestone, L.F. Bjeldanes, J. Biol. Chem. 278 (2003) 21136.
31. a) C. Grubbs, V. Steele, T. Casebolt, M.M. Juliana, I. Eto, L.M. Whitaker, Anticancer Res. 15 (1995) 709;
32. b) G.S. Bailey, R.H. Dashwood, A.T. Fong, D.E. Williams, R.A. Scalan, J.D. Hendriks, Anticancer Res. 78 (1991) 275;
33. c) T. Kojima, T. Tanaka, H. Mori, Cancer Res. 54 (1994) 1446;
34. d) H.G. Shertzer, M.W. Tabor, I.T. Hogan, S.J. Brown, M. Sainsbury, Arch. Toxicol. 70 (1996) 830;
35. e) M.B. Amao, J. Sanchez-Bravo, M. Acosta Biochem. Mol. Biol. Int. 39 (1996) 1125.
36. S.H. Benabadji, R. Wen, J. Zheng, X. Dong, S. Yuan, Acta Pharmacol. Sin. 25 (2004) 666.
37. X. Ge, S. Yannai, G. Rennert, N. Gruener, F.A. Fares, Biochem. Biophys. Res. Commun. 228 (1996) 153.
38. A. Kamal, A.A. Qureshi, Tetrahedron 19 (1963) 513.
39. a) P.K. Prandhan, S. Dey, V.S. Giri, P. Jaisankar, Synthesis (2005) 1779;
40. b) M.A. Zolfigol, P. Salehi, M. Shiri, Phosph. Sulfur Silic. 179 (2004) 2273;
41. c) Z.H. Zhang, L. Yin, Y.M. Wang, Synthesis (2005) 1949 and references sited therein.
42. a) M. Karthik, A.K. Tripathi, N.M. Gupta, M. Palanichamy, V. Murugesan, Catal. Commun. 5 (2004) 371;
43. b) M. Chakrabary, S. Sarkar, Tetrahedron Lett. 43 (2002) 1351;
44. c) C.J. Magesh, R. Nagarajan, M. Karthik, P.T. Perumal, Appl. Catal., A 266 (2004) 1;
45. d) S.A. Farhanullah, P.R. Maulik, V.J. Ram, Tetrahedron Lett. 45 (2004) 5099;
46. e) J. Li, M. Zhou, B.G. Li, G.L. Zhang, Synth. Commun. 34 (2004) 275.
47. a) S.J. Ji, S.Y. Wang, Y. Zhang, T.P. Loh, Tetrahedron 60 (2004) 2051;
48. b) B.P. Bandgar, K.A. Shaikh, Tetrahedron Lett. 44 (2003) 1959.
49. H. Koshima, W. Matsuaka, J. Heterocycl. Chem. 39 (2002) 1089.
50. R. Nagarajan, P.T. Perumal, Chem. Lett. 33 (2004) 288.
51. C. Ramesh, N. Ravindranath, B. Das, J. Chem. Res. (S) (2003) 72.
52. B.P. Bandgar, S.V. Bettigeri, N.S. Joshi, Monatsh. Chem. 135 (2004) 1265.
53. a) V. Bailleux, L. Vallee, J.P. Nuyts, J. Vamecq, Chem. Pharm. Bull. 42 (1994) 1817;
54. b) M.K. Hargreaves, J.G. Pritchard, H.R. Dave, Chem. Rev. 70 (1970) 439;
55. c) Y. Shibata, K. Sasaki, Y. Hashimoto, S. Iwasaki, Chem. Pharm. Bull. 44 (1996) 156.
56. a) S.B. Mhaske, N.P. Argade, Synthesis (2003) 863;
57. b) L.M. Lima, P. Castro, A.L. Machado, C.A.M. Fraga, C. Lugnier, V.L.G. Moreas, E. Barreiro, J. Bioorg. Med. Chem. 10 (2002) 3067;
58. c) S. Chandrasekhar, M.B. Padamaja, A. Raza, Synlett (1999) 1597.
59. R. Jayakumar, R. Balaji, S. Nanjundan, Eur. Polym. J. 36 (2000) 1659.
60. a) J.M. Chapman, P.J. Vorstad, G.H. Cocolas, I.H. Hall, J. Med. Chem. 26 (1983) 237;
61. b) A.S. Kalgutkar, B.C. Crew, L.J. Marnett, J. Med. Chem. 39 (1996) 1692;
62. c) P. Garne, W.B. Ho, S.K. Grandhee, W.J. Youngs, V.O. Kennedy, J. Org. Chem. 56 (1991) 5893.
63. a) J.S. Wilkes, J. Mol. Catal. A 214 (2004) 11;
64. b) N. Jain, A. Kumar, S. Chauhan, S.M.S. Chauhan, Tetrahedron 61 (2005) 1015.
65. a) A.C. Cole, J.L. Jensen, I. Ntai, K.L.T. Tran, K.J. Weaver, D.C. Forbes, J.H.J. Davis, J. Am. Chem. Soc. 124 (2002) 5962;
66. b) C. Thomazeau, H. Olivier-Bourbigou, L. Magna, S. Luts, B. Gilbert, J. Am. Chem. Soc. 125 (2003) 5264;
67. c) T. Joseph, S. Sahoo, S.B. Halligudi, J. Mol. Catal. A Chem. 234 (2005) 107;
68. d) Q. Cai, J. Li, F. Bao, Y. Shan, Appl. Catal. A Gen. 279 (2005) 139;
69. e) Z. Du, Z. Li, Y. Gu, J. Zhang, Y. Deng, J. Mol. Catal. A Chem. 237 (2005) 80.
70. G. Zhao, T. Jiang, H. Gao, B. Han, J. Huang, D. Sun, Green Chem. 6 (2004) 75.
71. a) M. Baghbanzadeh, P. Salehi, M. Dabiri, Gh. Kozehgary, Synthesis (2006) 344;
72. b) P. Salehi, M. Dabiri, A.R. Khosropour, P. Roozbehniya, J. Iran. Chem. Soc. 3 (2006) 98;
73. c) P. Salehi, M. Dabiri, M.A. Zolfigol, M.A. Bodaghi Fard, Tetrahdron Lett. 44 (2003) 2889;
74. d) P. Salehi, M. Dabiri, M.A. Zolfigol, M. Baghbanzadeh, Heterocycles 62 (2005) 1417;
75. e) M. Dabiri, P. Salehi, A.A. Mohammadi, M. Baghbanzadeh, Synth. Commun. 35 (2005) 279;
76. f) M. Dabiri, P. Salehi, S. Otokesh, M. Baghbanzadeh, Gh. Kozehgary, A.A. Mohammadi, Tetrahedron Lett. 46 (2005) 6123;
77. g) P. Salehi, M. Dabiri, M.A. Zolfigol, M. Baghbanzadeh, Tetrahdron Lett. 46 (2005) 7051;
78. h) P. Salehi, M. Dabiri, M.A. Zolfigol, S. Otokesh, M. Baghbanzadeh, Tetrahedron Lett. 47 (2006) 2557;
79. i) P. Salehi, M. Dabiri, M. Baghbanzadeh, M. Bahramnejad, Synth. Commun. 36 (2006) 2287;
80. j)M. Dabiri, P. Salehi, M. Baghbanzadeh, M. Bahramnejad, Tetrahedron Lett. 47 (2006) 6983.
81. T.U. Mayer, T.M. Kapoor, S.J. Haggarty, R.W. King, S.L. Schreiber, T. Mitchison, Science 286 (1999) 971.
82. a) B.M. Barchin, A.M. Cuadro, A.B. Julio, Synlett (2002) 343;
83. b) S. Chandrasekhar, N.B. Padmaja, A. Raza, Synlett (1999) 1597;
84. c) T. Vidal, A. Petit, A. Loupy, R.N. Gedye, Tetrahedron 56 (2000) 5473.
85. P.Y. Reddy, S. Kondo, T. Toru, Y. Ueno, J. Org. Chem. 62 (1997) 2652.
86. R.G.R. Bacon, A. Korim, J. Chem. Soc., Perkin Trans. 1 (1973) 272.
87. P. Jacquignon, N.P. Buu-Hoi, Bull. Soc. Chim. Fr. (1957) 935.