Facile and one-pot access of 3,3-bis(indol-3-yl)indolin-2-ones and 2,2-bis(indol-3-yl)acenaphthylen-1(2H)-one derivatives via an eco- friendly pseudo-multicomponent reaction at room temperature using sulfamic acid as an organo-catalyst

ACS Sustainable Chemistry and Engineering

Volumn 2, Issue 12, 2014, Pages 2802-2812

  Brahmachari, Goutam ^a   Banerjee, Bubun ^a  

^a VISVA BHARATI UNIVERSITY   (India)

Author keywords

Aqueous ethanol; Bis indolyl derivatives; Chemoselectivity; Green and sustainable chemistry; Medicinal chemistry; Multicomponent reactions; No column chromatography; Room temperature; Sulfamic acid

Indexed keywords

CATALYSTS; COLUMN CHROMATOGRAPHY; ETHANOL; LIQUID CHROMATOGRAPHY; NOBELIUM; REACTION KINETICS; REUSABILITY; SULFAMIC ACID; SYNTHESIS (CHEMICAL);

AQUEOUS ETHANOL; CHEMO-SELECTIVITY; GREEN AND SUSTAINABLE CHEMISTRIES; MEDICINAL CHEMISTRY; MULTI-COMPONENT REACTIONS; ROOM TEMPERATURE;

CHROMATOGRAPHY;

EID: 84928468056     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc500575h     Document Type: Article

References (110)

1. Rahman, A.; Basha, A. Indole Alkaloids; Harwood Academic Publishers: Chichester, U.K., 1998.
2. Faulkner, D. J. Marine natural products. Nat. Prod. Rep. 2000, 17, 7-55.
3. Ninomiya, I. Recent progress in the synthesis of indole alkaloid. J. Nat. Prod. 1992, 55, 541-564.
4. Chao, W. R.; Yean, D.; Amin, K.; Green, C.; Jong, L. Computeraided rational drug design: A novel agent (SR13668) designed to mimic the unique anticancer mechanisms of dietary indole-3-carbinol to block akt signaling. J. Med. Chem. 2007, 50, 3412-3415.
5. Andreani, A.; Burnelli, S.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Varoli, L.; Landi, L.; Prata, C.; Berridge, M. V.; Grasso, C.; Fiebig, H. H.; Kelter, G.; Burger, A. M.; Kunkel, M. W. Antitumor activity of bis-indole derivatives. J. Med. Chem. 2008, 51, 4563-4570.
6. Giannini, G.; Marzi, M.; Marzo, M. D.; Battistuzzi, G.; Pezzi, R.; Brunetti, T.; Cabri, W.; Vesci, L.; Pisano, C. Exploring bis- (indolyl)methane moiety as an alternative and innovative CAP group in the design of histone deacetylase (HDAC) inhibitors. Bioorg. Med. Chem. Lett. 2009, 19, 2840-2843.
7. Shiri, M.; Zolfigol, M. A.; Kruger, H. G.; Tanbakouchian, Z. Bisand trisindolylmethanes (BIMs and TIMs). Chem. Rev. 2010, 110, 2250-2293.
8. Gaisina, I. N.; Gallier, F.; Ougolkov, A. V.; Kim, K. H.; Kurome, T.; Guo, S.; Holzle, D.; Luchini, D. N.; Blond, S. Y.; Billadeau, D. D.; Kozikowski, A. P. From a natural product lead to the identification of potent and selective benzofuran-3-yl-(indol-3-yl)maleimides as glycogen synthase kinase 3β inhibitors that suppress proliferation and survival of pancreatic cancer cells. J. Med. Chem. 2009, 52, 1853-1863.
9. Queiroz, M. R. P.; Abreu, A. S.; Carvalho, M. S. D.; Ferreira, P. M. T.; Nazareth, N.; Nascimento, M. S.-J. Synthesis of new heteroaryl and heteroannulated indoles from dehydrophenylalanines: Antitumor evaluation. Bioorg. Med. Chem. 2008, 16, 5584-5589.
10. Vine, K. L.; Matesic, L.; Locke, J. M.; Ranson, M.; Skropeta, D. Cytotoxic and anticancer activities of isatin and its derivatives: A comprehensive review from 2000-2008. Anticancer Agents Med. Chem. 2009, 9, 397-414.
11. Kobayashi, M.; Aoki, S.; Gato, K.; Matsunami, K.; Kurosu, M.; Kitagawa, I. Marine Natural Products. XXXIV. Trisindoline, a new antibiotic indole trimer, produced by bacterium of Vibrio sp. separated from the marine sponge Hyrtios altum. Chem. Pharm. Bull. 1994, 42, 2449-2451.
12. Veluri, R.; Oka, I.; Wagner-Döbler, I.; Laatsch, H. New indole alkaloids from the North Sea bacterium Vibrio parahaemolyticus Bio249. J. Nat. Prod. 2003, 66, 1520-1523.
13. Loo, Y. H.; Woolf, D. O. Microbiological oxidation of indole. Chem. Ind. 1957, 1123.
14. Bell, R.; Carmeli, S. Vibrindole A, a metabolite of the marine bacterium, Vzbrzo parahaemolytzcus, isolated from the toxic mucus of the boxfish Ostraczon cubzcus. J. Nat. Prod. 1994, 57, 1587-1590.
15. Khuzhaev, V. U.; Zhalolov, I.; Turguniv, K. K.; Tashkhodzhaev, B.; Levkovich, M. G.; Arpova, S. F.; Shashkov, A. S. Alkaloids from Arundo donax: XVII. Structure of the dimeric indole alkaloid arundaphine. Chem. Nat. Compd. 2004, 40, 269-272.
16. Rasmussen, H. B.; MacLeod, J. K. Total synthesis of donaxaridine. J. Nat. Prod. 1997, 60, 1152-1154.
17. Kagata, T.; Saito, S.; Shigemori, H.; Ohsaki, A.; Ishiyama, H.; Kubota, T.; Kobayashi, J. Paratunamides A-D, oxindole alkaloids from Cinnamodendron axillare. J. Nat. Prod. 2006, 69, 1517-1521.
18. Tang, Y. Q.; Sattler, I.; Thiericke, R.; Grabley, S.; Feng, X. Z. Maremycins C and D, new diketopiperazines, and maremycins E and F, novel polycyclic spiro-indole metabolites isolated from Streptomyces sp. Eur. J. Org. Chem. 2001, 66, 261-267.
19. Kamano, Y.; Zhang, H. P.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Itokawa, H.; Pettit, G. R. Convolutamydine A, a novel bioactive hydroxyoxindole alkaloid from marine bryozoan Amathia convolute. Tetrahedron Lett. 1995, 36, 2783-2784.
20. Goehring, R. R.; Sachdeva, Y. P.; Pisipati, J. S.; Sleevi, M. C.; Wolfe, J. F. Photo-induced cyclizations of mono- And dianions of Nacyl- o-chloroanilines and N-acyl-o-chlorobenzylamines as general methods for the synthesis of oxindoles and 1, 4-dihydro-3(2H)- isoquinolinones. J. Am. Chem. Soc. 1985, 107, 435-443.
21. Galliford, C. V.; Scheidt, K. A. Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents. Angew. Chem., Int. Ed. 2007, 46, 8748-8758.
22. Kulkarni, M. G.; Dhondge, A. P.; Chavhan, S. W.; Borhade, A. S.; Shaikh, Y. B.; Birhade, D. R.; Desai, M. P.; Dhatrak, N. R. Total synthesis of (±)-coerulescine and (±)-horsfiline. Beilstein J. Org. Chem. 2010, 6, 876-879.
23. Lin, H.; Danishefsky, S. J. Gelsemine: A thought-provoking target for total synthesis. Angew. Chem., Int. Ed. 2003, 42, 36-51.
24. Jensen, B. S. BMS-204352: A potassium channel opener developed for the treatment of stroke. CNS Drug Rev. 2002, 8, 353-360.
25. Joshi, K. C.; Pathak, V. N.; Jain, S. K. Studies of potential organo-fluorine antibacterial agents. Part 5: Synthesis and antibacterial activity of some new fluorine-containing indole-2, 3-dione derivatives. Pharmazie 1980, 35, 677-679.
26. Pajouhesh, H.; Parsons, R.; Popp, F. D. Potential anticonvulsants VI: condensation of isatins with cyclohexanone and other cyclic ketones. J. Pharm. Sci. 1983, 72, 318-321.
27. Denoyelle, S.; Chen, T.; Yang, H.; Chen, L.; Zhang, Y.; Halperin, J. A.; Aktas, B. H.; Chorev, M. Synthesis and SAR study of novel 3, 3-diphenyl-1, 3-dihydroindol-2-one derivatives as potent eIF2.GTP.Met-tRNAi Met ternary complex inhibitors. Eur. J. Med. Chem. 2013, 69, 537-553.
28. Natarajan, A.; Guo, Y.; Harbinski, F.; Fan, Y. H.; Chen, H.; Luus, L.; Diercks, J.; Aktas, H.; Chorev, M.; Halperin, J. A. Novel arylsulfoanilide-oxindole hybrid as an anticancer agent that inhibits translation initiation. J. Med. Chem. 2004, 47, 4979-4982.
29. Chiyanzu, I.; Clarkson, C.; Smith, P. J.; Lehman, J.; Gut, J.; Rosenthalc, P. J.; Chibale, K. Design, synthesis and anti-plasmodial evaluation in vitro of new 4-aminoquinoline isatin derivatives. Bioorg. Med. Chem. 2005, 13, 3249-3261.
30. Jiang, T.; Kuhen, K. L.; Wolff, K.; Yin, H.; Bieza, K.; Caldwell, J.; Bursulaya, B.; Tuntland, T.; Zhang, K.; Karanewsky, D.; He, Y. Design, synthesis, and biological evaluations of novel oxindoles as HIV-1 nonnucleoside reverse transcriptase inhibitors. Part 2. Bioorg. Med. Chem. Lett. 2006, 16, 2109-2112.
31. Sridhara, S. K.; Saravanana, M.; Ramesh, A. Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives. Eur. J. Med. Chem. 2001, 36, 615-625.
32. Cane, A.; Tournaire, M.-C.; Barritault, D.; Crumeyrolle-Arias, M. The endogenous oxindoles 5-hydroxyoxindole and isatin are antiproliferative and proapoptotic. Biochem. Biophys. Res. Commun. 2000, 276, 379-384.
33. Silveira, V. Ch; Luz, J. S.; Oliveira, C. C.; Graziani, I.; Ciriolo, M. R.; Costa Ferreira, A. M. Double-strand DNA cleavage induced by oxindole-Schiff base copper(II) complexes with potential antitumor activity. J. Inorg. Biochem. 2008, 102, 1090-1103.
34. Raj, A. A.; Raghunathan, R.; Sridevikumaria, M. R.; Raman, N. Synthesis, antimicrobial and antifungal activity of a new class of spiro pyrrolidines. Bioorg. Med. Chem. 2003, 11, 407-419.
35. Rodriguez-Arguelles, M. C.; Mosquera-Vazaquez, S.; Touron- Touceda, P.; Sanmartin- Matalobos, J.; Garcia-Deibe, A. M.; Belicchi- Ferraris, M.; Pelosi, G.; Pelizzi, C.; Zani, F. Complexes of 2- Thiophenecarbonyl and isonicotinoyl hydrazones of 3-(N-methyl)- isatin. A study of their antimicrobial activity. J. Inorg. Biochem. 2007, 101, 138-147.
36. Maskell, L.; Blanche, E. A.; Colucci, M. A.; Whatmore, J. L.; Moody, Ch. J. Synthesis and evaluation of prodrugs for anti-angiogenic pyrrolylmethylidenyl oxindoles. Bioorg. Med. Chem. Lett. 2007, 17, 1575-1578.
37. Verma, M.; Nath Pandeya, S.; Nand Singh, K.; Stables, J. P. Anticonvulsant activity of Schiff bases of isatin derivatives. Acta Pharm. 2004, 54, 49-56.
38. Igosheva, N.; Lorz, C.; O'Conner, E.; Glover, V.; Mehmet, H. Isatin, an endogenous monoamine oxidase inhibitor, triggers a doseand time-dependent switch from apoptosis to necrosis in human neuroblastoma cells. Neurochem. Int. 2005, 47, 216-224.
39. Chen, L.-R.; Wang, Y.-Ch.; Lin, Y. W.; Chou, Sh.-Y.; Chen, Sh.- F.; Liu, L. T.; Wu, Y.-T.; Kuo, Ch.-J.; Chen, T. Sh.-Sh.; Juang, Sh.-H. Synthesis and evaluation of isatin derivatives as effective SARS coronavirus 3CL protease inhibitors. Bioorg. Med. Chem. Lett. 2005, 15, 3058-3062.
40. Natarajan, A.; Fan, Y. H.; Chen, H.; Guo, Y.; Iyasere, J.; Harbinski, F.; Christ, W. J.; Aktas, H.; Halperin, J. A. 3, 3-Diaryl- 1, 3- dihydroindol-2-ones as antiproliferatives mediated by translation initiation inhibition. J. Med. Chem. 2004, 47, 1882-1885.
41. Bal, R. T.; Anand, B.; Yogeeswari, P.; Sriram, D. Synthesis and evaluation of anti-HIV activity of isatin β-thiosemicarbazone derivatives. Bioorg. Med. Chem. Lett. 2005, 15, 4451-4455.
42. Tripathy, R.; Reiboldt, A.; Messina, P. A.; Iqbal, M.; Singh, J.; Bacon, E. R.; Angeles, Th. S.; Yang, Sh. X.; Albom, M. S.; Robinson, C.; Chang, H.; Ruggeri, B. A.; Mallamo, J. P. Structure-guided identification of novel VEGFR-2 kinase inhibitors via solution phase parallel synthesis. Bioorg. Med. Chem. Lett. 2006, 16, 2158-2162.
43. Paira, P.; Hazra, A.; Kumar, S.; Paira, R.; Sahu, K. B.; Naskar, S.; Saha, P.; Mondal, S.; Maity, A.; Banerjee, S.; Mondal, N. B. Efficient synthesis of 3, 3-diheteroaromatic oxindole analogues and their in vitro evaluation for spermicidal potential. Bioorg. Med. Chem. Lett. 2009, 19, 4786-4789.
44. Kamal, A.; Srikanth, Y. V. V; Khan, M. N. A.; Shaik, T. B.; Ashraf, M. Synthesis of 3, 3-diindolyl oxyindoles efficiently catalysed by FeCl3 and their in vitro evaluation for anticancer activity. Bioorg. Med. Chem. Lett. 2010, 20, 5229-5231.
45. Reddy, B.V. S.; Rajeswari, N.; Sarangapani, M.; Prashanthi, Y.; Ganji, R. J.; Addlagatta, A. Iodine-catalyzed condensation of isatin with indoles: A facile synthesis of di(indolyl)indolin-2-ones and evaluation of their cytotoxicity. Bioorg. Med. Chem. Lett. 2012, 22, 2460-2463.
46. Sarrafi, Y.; Alimohammadi, K.; Sadatshahabi, M.; Norozipoor, N. An improved catalytic method for the synthesis of 3, 3-di(indolyl)- oxindoles using Amberlyst 15 as a heterogeneous and reusable catalyst in water. Monatsh. Chem. 2012, 143, 1519-1522.
47. Alimohammadi, K.; Sarrafi, Y.; Tajbakhsh, M. H6P2W18O62: A green and reusable catalyst for the synthesis of 3, 3-diaryloxindole derivatives in water. Monatsh. Chem. 2008, 139, 1037-1039.
48. Alinezhad, H.; Haghighi, A. H.; Salehian, F. A green method for the synthesis of bis-indolylmethanes and 3, 3′-indolyloxindole derivatives using cellulose sulfuric acid under solvent-free conditions. Chin. Chem. Lett. 2010, 21, 183-186.
49. Patel, G. M.; Deota, P. T. Tungstic acid-catalyzed synthesis of 3, 3-bis(1H-indol-3-yl)indolin-2-one derivatives. Heterocycl. Commun. 2013, 19, 421-424.
50. Nikpassand, M.; Mamaghani, M.; Tabatabaeian, K.; Samimi, H. A. An efficient and clean synthesis of symmetrical and unsymmetrical 3, 3-di(indolyl)indolin-2-ones using KSF. Synth. Commun. 2010, 40, 3552-3560.
51. Wang, S.-Y.; Ji, S.-J. Facile synthesis of 3, 3-di(heteroaryl)indolin- 2-one derivatives catalyzed by ceric ammonium nitrate (CAN) under ultrasound irradiation. Tetrahedron 2006, 62, 1527-1535.
52. Chakrabarty, M.; Sarkar, S.; Harigaya, Y. A facile clay-mediated synthesis of 3, 3-diindolyl-2-indolinones from isatins. J.Chem. Res. 2005, 540-542.
53. Azizian, J.; Mohammadi, A. A.; Karimi, A. R.; Mohammadizadeh; Mohammad, R. KAl(SO4)2.12H2O as a recyclable Lewis acid catalyst for synthesis of some new oxindoles in aqueous media. J. Chem. Res. 2004, 424-426.
54. Naskar, S.; Saha, P.; Paira, R.; Paira, P.; Hazra, A.; Sahu, K. B.; Banerjee, S.; Mondal, N. B. Aqueous phase supramoleculer synthesis of 3, 2- And 3, 3-dihetero-aromatic oxindoles catalysed by β-cyclodextrin. J. Chem. Res. 2009, 174-177.
55. Guoliang, F.; Lijun, G.; Hongli, Z. Facile synthesis of 3, 3- di(indolyl)indolin-2-one derivatives catalyzed by ZrO2/S2O8 2- solid superacid under grinding condition. Chem. J. Internet 2009, 11, 1 (111001pe).
56. Rad-Moghadam, K.; Sharifi-Kiasaraie, M.; Taheri-Amlashi, H. Synthesis of symmetrical and unsymmetrical 3, 3-di(indolyl)indolin-2- ones under controlled catalysis of ionic liquids. Tetrahedron 2010, 66, 2316-2321.
57. Narges, K.; Hooesin, O.; Majid, H.; Mina, S.; Masoumeh, Z.; Niloofar, T. On water: Brønsted acidic ionic liquid [(CH2)4SO3HMIM][HSO4] catalyzed synthesis of oxindoles derivatives. Chin. J. Chem. 2011, 29, 321-323.
58. Sharma, R. K.; Sharma, C. A highly efficient synthesis of oxindoles using a functionalized silica gel as support for indium(III) acetylacetonate catalyst in an aqueous-acetonitrile medium. J. Mol. Catal. A: Chem. 2010, 332, 53-58.
59. Harbison, G. S.; Kye, Y.-S.; Penner, G. H.; Grandin, M.; Monette, M. 14N quadrupolar, 14N and 15N chemical shift, and 14N-1H dipolar tensors of sulfamic acid. J. Phys. Chem. B 2002, 160, 10285- 10291.
60. Yang, J.; Zhang, J.; Chen, T. T.; Sun, D. M.; Li, J.; Wu, X. F. Sulfamic acid as a cost-effective and recyclable solid acid catalyst for Friedel-Crafts alkylation of indole with α, β-unsaturated carbonyl compound and benzyl alcohol. Chin. Chem. Lett. 2011, 22, 1391-1394.
61. Rostami, A.; Ahmad-Jangi, F. Sulfamic acid: An efficient, costeffective and green catalyst for crossed-aldol condensation of ketones with aromatic aldehydes under solvent-free. Chin. Chem. Lett. 2011, 22, 1029-1032.
62. An, L.-T.; Zou, J.-P.; Zhang, L.-L.; Zhang, Y. Sulfamic acidcatalyzed Michael addition of indoles and pyrrole to electron-deficient nitroolefins under solvent-free condition. Tetrahedron Lett. 2007, 48, 4297-4300.
63. Zeng, H.; Li, H.; Shao, H. One-pot three-component Mannichtype reactions using Sulfamic acid catalyst under ultrasound irradiation. Ultrason. Sonochem. 2009, 16, 758-762.
64. Xia, M.; Lu, Y.-D. A novel direct and one-pot Mannich synthesis of fluorinated β-aminobutanones with sulfamic acid as a green catalyst. J. Fluorine Chem. 2006, 127, 1119-1124.
65. Luo, H.-T.; Kang, Y.-R.; Nie, H.-Y.; Yang, L.-M. Sulfamic acid as a cost effective and recyclable catalyst for β-amino carbonyl compounds synthesis. J. Chin. Chem. Soc. 2009, 56, 186-195.
66. Heydari, A.; Khaksar, S.; Pourayoubi, M.; Mahjoub, A. R. Sulfamic acid: An efficient, cost-effective and recyclable solid acid catalyst for the three-component synthesis of α-aminonitriles. Tetrahedron Lett. 2007, 48, 4059-4060.
67. Chen, W. Y.; Qin, S. D.; Jin, J. R. Efficient Biginelli reaction catalyzed by sulfamic acid or silica sulfuric acid under solvent-free conditions. Synth. Commun. 2007, 37, 47-52.
68. Wu, L.; Zhang, C.; Li, W. Regioselective synthesis of 6-arylbenzo[ h][1, 2, 4] triazolo[5, 1-b]quinazoline-7, 8-diones as potent antitumoral agents. Bioorg. Med. Chem. Lett. 2013, 23, 5002-5005.
69. Li, J.; Qiu, J.; Li, H.; Zhang, G. An efficient, three-component one-pot preparation of 1, 4-dihydropyridines containing novel substituted pyrazole under sulfamic acid catalysis. Chin. J. Chem. 2011, 29, 511-514.
70. Shinde, S. V.; Jadhav, W. N.; Kondre, J. M.; Gampawar, S. V.; Karade, N. N. Sulfamic acid catalysed one-pot three-component condensation for the synthesis of 1, 4-dihydropyrano[2, 3-c]pyrazoles. J. Chem. Res. 2008, 278-279.
71. D'Oca, M. G. M.; Soares, R. M.; de Moura, R. R.; Granjão, V. de F. Sulfamic acid: An efficient acid catalyst for esterification of FFA. Fuel 2012, 97, 884-886.
72. Heravi, M. M.; Ranjbar, L.; Derikvand, F.; Alimadadi, B. Three component one-pot synthesis of 4, 6-diarylpyrimidin-2(1H)-ones under solvent-free conditions in the presence of sulfamic acid as a green and reusable catalyst. Mol. Divers 2008, 12, 191-196.
73. Heravi, M. M.; Baghernejad, B.; Oskooie, H. A. Application of sulfamic acid in organic synthesis-A short review. Current Org. Chem. 2009, 13, 1002-1014.
74. Heravi, M. M.; Alinejhad, H.; Bakhtiari, K.; Oskooie, H. A. Sulfamic acid catalyzed solvent-free synthesis of 10-aryl-7, 7-dimethyl- 6, 7, 8, 10-tetrahydro-9H-[1, 3]-dioxolo[4, 5-b]xanthen-9-ones and 12- Aryl-9, 9-dimethyl-8, 9, 10, 12-tetrahydro-11H-benzo[a]xanthen-11-ones. Mol. Divers. 2010, 14, 621-626.
75. Arya, A. K.; Gupta, S. K.; Kumar, M. A domino protocol for the efficient synthesis of structurally diverse benzothiazolylquinoline-2, 5- diones and their spiro analogues. Tetrahedron Lett. 2012, 53, 6035- 6038.
76. Moradi, L.; Piltan, M.; Rostami, H.; Abasi, G. One-pot synthesis of pyrrolo[1, 2-α]pyrazines via three component reaction of ethylenediamine, acetylenic esters and nitrostyrene derivatives. Chin. Chem. Lett. 2013, 24, 740-742.
77. Yadav, J. S.; Rao, P. P.; Sreenu, D.; Rao, R. S.; Kumar, V. N.; Nagaiah, K.; Prasad, A. R. Sulfamic acid: An efficient, cost-effective and recyclable solid acid catalyst for the Friedlander quinoline synthesis. Tetrahedron Lett. 2005, 46, 7249-7253.
78. Wang, B.; Gu, Y.; Gong, W.; Kang, Y.; Yang, L.; Suo, J. Sulfamic acid as a cost-effective catalyst instead of metal-containing acids for acetolysis of cyclic ethers. Tetrahedron Lett. 2004, 45, 6599-6602.
79. Cariou, C. C. A.; Clarkson, G. J.; Shipman, M. Rapid synthesis of 1, 3, 4, 4-tetrasubstituted β-lactams from methyleneaziridines using a four-component reaction. J. Org. Chem. 2008, 73, 9762-9764.
80. Verma, A. K.; Kotla, S. K. R.; Choudhary, D.; Patel, M.; Tiwari, R. K. Silver-catalyzed tandem synthesis of naphthyridines and thienopyridines via three-component reaction. J. Org. Chem. 2013, 78, 4386-4401.
81. Singh, M. S.; Chowdhury, S. Recent developments in solventfree multicomponent reactions: A perfect synergy for eco-compatible organic synthesis. RSC Adv. 2012, 2, 4547-4592.
82. Mukhopadhyay, C.; Tapaswi, P. K.; Drew, M. G. B. Room temperature synthesis of tri-, tetrasubstituted imidazoles and bisanalogues by mercaptopropylsilica (MPS) in aqueous methanol: Application to the synthesis of the drug trifenagrel. Tetrahedron Lett. 2010, 51, 3944-3950.
83. Kumaravel, K.; Vasuki, G. Multi-component reactions in water. Curr. Org. Chem. 2009, 13, 1820-1841.
84. Brauch, S.; Gabriel, L.; Westermann, B. Seven-component reactions by sequential chemoselective Ugi-Mumm/Ugi-Smiles reactions. Chem. Commun. 2010, 46, 3387-3389.
85. Pellissier, H. Stereocontrolled domino reactions. Chem. Rev. 2013, 113, 442-524.
86. Brauch, S.; Berkel, S. S. V.; Westermann, B. Higher-order multicomponent reactions: Beyond four reactants. Chem. Soc. Rev. 2013, 42, 4948-4962.
87. Pastori, N.; Gambarotti, C.; Punta, C. Recent developments in nucleophilic radical addition to imines: The key role of transition metals and the new porta radical type version of the Mannich and Strecker reactions. Mini-Rev. Org. Chem. 2009, 6, 184-195.
88. Hafez, E. A. A.; Al-Mousawi, S. M.; Moustafa, M. S.; Sadek, K. U.; Elnagdi, M. H. Green methodologies in organic synthesis: Recent developments in our laboratories. Green Chem. Lett. Rev. 2013, 6, 189-210.
89. Clerici, A.; Ghilardi, A.; Pastori, N.; Punta, C.; Porta, O. A new one-pot, four-component synthesis of 1, 2-amino alcohols: TiCl3/t- BuOOH-mediated radical hydroxymethylation of imines. Org. Lett. 2008, 10, 5063-5066.
90. Pastori, N.; Greco, C.; Clerici, A.; Punta, C.; Porta, O. Freeradical addition to ketimines generated in situ. New one-pot synthesis of quaternary α-aminoamides promoted by a H2O2/TiCl4-Zn/HCONH2 system. Org. Lett. 2010, 12, 3898-3901.
91. Khurana, J. M.; Chaudhary, A.; Lumb, A.; Nand, B. An expedient four-component domino protocol for the synthesis of novel benzo[a]phenazine annulated heterocycles and their photophysical studies. Green Chem. 2012, 14, 2321-2327.
92. Prasad, D.; Nath, M. Three-component domino reaction in PPG: An easy access to 4-thiazolidinone derivatives. J. Heterocyclic Chem. 2012, 49, 628-633.
93. Trost, B. M. The atom economy-A search for synthetic efficiency. Science 1991, 254, 1471-1477.
94. Sheldon, R. A. Atom efficiency and catalysis in organic synthesis. Pure Appl. Chem. 2000, 72, 1233-1246.
95. Brahmachari, G.; Laskar, S. A very simple and highly efficient procedure for N-formylation of primary and secondary amines at room temperature under solvent-free conditions. Tetrahedron Lett. 2010, 51, 2319-2322.
96. Brahmachari, G.; Laskar, S.; Sarkar, S. Metal acetate/metal oxide in acetic acid: An efficient reagent for the chemoselective N-acetylation of amines. J. Chem. Res. 2010, 34, 288-295.
97. Brahmachari, G.; Laskar, S.; Sarkar, S. A green approach to chemoselective N-acetylation of amines using catalytic amount of zinc acetate in acetic acid under microwave irradiation. Indian J. Chem. 2010, 49B, 1274-1281.
98. Brahmachari, G.; Das, S. Bismuth nitrate-catalyzed multicomponent reaction for efficient and one-pot synthesis of densely functionalized piperidine scaffolds at room temperature. Tetrahedron Lett. 2012, 53, 1479-1484.
99. Brahmachari, G.; Banerjee, B. A comparison between catalystfree and ZrOCl2·8H2O-catalyzed Strecker reactions for the rapid and solvent-free one-pot synthesis of racemic α-aminonitrile derivatives. Asian J. Org. Chem. 2012, 1, 251-258.
100. Brahmachari, G.; Das, S. One-pot synthesis of 3-[(Nalkylanilino)( aryl)methyl] indoles via a transition metal assisted three component condensation at room temperature. J. Heterocyclic Chem. 2014, 51, E140-E145.
101. Brahmachari, G.; Das, S. Sodium formate-catalyzed one-pot synthesis of benzopyranopyrimidines and 4-thio-substituted 4Hcromenes via multicomponent reaction at room temperature. J. Heterocyclic Chem. 2014, in press, DOI: 10.1002/jhet.2123.
102. Das, S.; Brahmachari, G. Ni(ClO4)2.6H2O: An efficient catalyst for one-pot synthesis of densely functionalized piperidine scaffolds via multicomponent reaction in ethanol at room temperature. Singpost Open Access J. Org. Biomol. Chem. 2013, 1, 33-46.
103. Brahmachari, G.; Das, S. A simple and straightforward method for one-pot synthesis of 2, 4, 5-triarylimidazoles using titanium dioxide as an eco-friendly and recyclable catalyst under solvent-free conditions. Indian J. Chem. 2013, 52B, 387-393.
104. Brahmachari, G.; Banerjee, B. Facile synthesis of symmetrical bis(benzhydryl)ethers using p-toluenesulfonyl chloride under solvent free conditions. Org. Med. Chem. Lett. 2013, 1, 1 DOI: 10.1186/2191-2858-3-1.
105. Brahmachari, G.; Laskar, S.; Barik, P. Magnetically separable MnFe2O4 nano-material: An efficient and reusable heterogeneous catalyst for the synthesis of 2-substituted benzimidazoles and the extended synthesis of quinoxalines at room temperature. RSC Adv. 2013, 3, 14245-14253.
106. Brahmachari, G.; Laskar, S.; Banerjee, B. Eco-friendly, one-pot multicomponent synthesis of pyran annulated heterocyclic scaffolds at room temperature using ammonium or sodium formate as non-toxic catalyst. J. Heterocyclic Chem. 2014, 51, E303-E308.
107. Brahmachari, G.; Banerjee, B. Facile and one-pot access to diverse and densely functionalized 2-amino-3-cyano-4H-pyrans and pyran-annulated heterocyclic scaffolds via an eco-friendly multicomponent reaction at room temperature using urea as a novel organo-catalyst. ACS Sustainable Chem. Eng. 2014, 2, 411-422.
108. Brahmachari, G.; Das, S. L-Proline catalyzed multicomponent one-pot synthesis of gem-diheteroarylmethane derivatives using facile grinding operation under solvent-free conditions at room temperature. RSC Adv. 2014, 4, 7380-7388.
109. Brahmachari, G.; Laskar, S. Nano-Mgo-catalyzed one-pot synthesis of phosphonate ester functionalized 2-amino-3-cyano-4Hchromene scaffolds at room temperature. Phosphorus Sulfur Silicon Relat. Elem. 2014, DOI: 10.1080/10426507.2014.903484.
110. Complete crystallographic data of 5′-nitro-1H, 1″H-[3, 3′:3′, 3″- Terindol]-2′(1′H)-one (3q) (Table 2, entry 17) for the structural analysis have been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 1017941. Copies of this information may be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.