Abstract
An efficient, mild, and expeditious synthetic protocol has been developed for the synthesis of structurally diverse 3-amino-imidazo[1,2-a]pyridines, involving a three-component, one-pot cyclocondensation reaction of 2-aminobenzothiazole/2-aminoazines, ethyl isocyanoacetate/tert-butyl isocyanides, and pyrazole-3(4)-carbaldehyde/substituted aromatic carbonyl compounds in 45 min. using In(OTf)\(_{3}\) as a catalyst in toluene. Mild reaction conditions, high atom economy, operational simplicity, short reaction time, and structural diversity with high product conversion are among the advantages of the present synthetic protocol.
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References
Horton DA, Bourne TG, Smythe ML (2003) The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem Rev 103:893–930. doi:10.1021/cr020033s
Zhu JP, Bienaymè H (2005) Multicomponent reactions. Wiley-VCH Weinheim, Dresden
Dömling A, Wang W, Wang K (2012) Chemistry and biology of multicomponent reactions. Chem Rev 112:3083–3135. doi:10.1021/cr100233r
Krasavin M, Tsirulnikov S, Nikulnikov M, Sandulenko Y, Bukhryakov K (2008) tert-Butyl isocyanide revisited as a convertible reagent in the Groebke–Blackburn reaction. Tetrahedron Lett 49:7318–7321. doi:10.1016/j.tetlet.2008.06.113
Domling A (2000) The discovery of new isocyanide based multicomponent reactions. Curr Opin Chem Biol 4:318–323. doi:10.1016/s1367-5931(00)00095-8
Devi N, Rawal RK, Singh V (2015) Diversity-oriented synthesis of fused-imidazole derivatives via Groebke–Blackburn–Bienayme reaction: a review. Tetrahedron 71:182–232. doi:10.1016/j.tet.2014.10.032
Dandia A, Jain AK, Sharma S (2012) Indium triflate catalyzed one pot multicomponent synthesis of spiro-hexahydropyrimidines explained by multiple covalent bond formation. Tetrahedron Lett 53:5270–5274. doi:10.1016/j.tetlet.2012.07.079
Karami B, Khodabakhshi S, Karamia S (2014) Indium(III) Trifluoromethanesulfonate: a reusable catalyst for the solvent-free synthesis of some quinazolinones/thiones. Croat Chem Acta 87:23–27. doi:10.5562/cca2087B
Dombroski MA, Letavic MA, McClure KF (2002) Benzimidazole anti-inflammatory compounds. WO 2002072576:A1
Sanghai N, Jain V, Preet R, Kandekar S, Das S, Trivedi N, Mohapatra P, Priyadarshani G, Kashyap M, Das D, Satapathy SR, Siddharth S, Guchhait SK, Kundu CN, Bharatamab PV (2014) Combretastatin A-4 inspired novel 2-aryl-3-arylamino-imidazo-pyridines/pyrazines as tubulin polymerization inhibitors, antimitotic and anticancer agents. Med Chem Comm 6:766–782. doi:10.1039/c3md00357d
Shukla NM, Salunke DB, Yoo E, Mutz CA, Balakrishna R, David SA (2012) Antibacterial activities of Groebke–Blackburn–Bienaymé-derived imidazo[1,2-\(a]\)pyridin-3-amines. Bioorg Med Chem 20:5850–5863. doi:10.1016/j.bmc.2012.07.052
Moraski GC, Markley LD, Hipskind PA, Boshofff H, Cho S, Franzblau SG, Miller MJ (2011) Advent of imidazo[1,2-\(a\)]pyridine-3-carboxamides with potent multi and extended drug resistant antituberculosis activity. ACS Med Chem Lett 2:466–470. doi:10.1021/ml200036r
Harrison TS, Keating GM (2005) Zolpidem: a review of its use in the management of insomnia. CNS Drugs 19:65–89. doi:10.2165/00023210-200519010-00008
Langer SZ, Arbilla S, Benavides J, Scatton B (1990) Zolpidem and alpidem: two imidazopyridines with selectivity for omega-1 and omega 3-receptor subtypes. Adv Biochem Psychopharmacol 46:61–72
Ueda T, Mizusgige K, Yukiiri K, Takahashi T, Kohno M (2003) Improvement of cerebral blood flow by olprinone, a phosphodiesterase-3 inhibitor, in mild heart failure. Cerebrovasc Dis 16:396–401. doi:10.1159/000072563
Altaf AA, Shahzad A, Gul Z, Rasool N, Badshah A, Lal B, Khan E (2015) A review on the medicinal importance of pyridine derivatives. J Drug Des Med Chem 1:1–11. doi:10.11648/j.jddmc.20150101.11
Mun EC, Mayol JM, Riegler M, O’Brien TC, Farokhzad OC, Song JC, Pothoulakis C, Hrnjez BJ, Matthews JB (1998) Levamisole inhibits intestinal Cl-secretion via basolateral K\(^{+}\) channel blockade. Gastroenterology 114:1257–1267. doi:10.1016/S0016-5085(98)70432-9
Sanger DJ (1995) Behavioral effects of novel benzodiazepine (omega) receptor agonists and partial agonists: increases in punished responding and antagonism of the pentylenetetrazole cue. Behav Pharmacol 6:116–126. doi:10.1097/00008877-199503000-00003
Damljanovic I, Vukicevi M, Radulovic N, Palic R, Ellmerer E, Ratkovic Z, Joksovic MD, Vukicevic RD (2009) Synthesis and antimicrobial activity of some new pyrazole derivatives containing a ferrocene unit. Bioorg Med Chem Lett 19:1093–1096. doi:10.1016/j.bmcl.2009.01.006
Pelling JC, Shipman C (1976) Antiviral activity of 2,3-hihydro-1\(H\) imidazo[1,2-\(b\)]pyrazole in simplex virus type-1 infected mammalian cells. Biochem Pharmacol 25:2377–2382. doi:10.1016/0006-2952(76)90031-9
Baviskar AT, Madaan C, Preet R, Mohapatra P, Jain V, Agarwal A, Guchhait SK, Kundu CN, Banerjee UC, Bharatam PV (2011) N-fused imidazoles as novel anticancer agents that inhibit catalytic activity of topoisomerase II alpha and induce apoptosis in G1/S phase. J Med Chem 54:5013–5030. doi:10.1021/jm200235u
Chovatia PT, Akabari JD, Kachhadia PK, Zalawadia PD, Joshi HS (2007) Synthesis and selective antitubercular and antimicrobial inhibitory activity of 1-acetyl-3,5-diphenyl-4,5-dihydro-(1h)-pyrazole derivatives. J Serb Chem Soc 71:713–420. doi:10.2298/JSC0607713C
Bekhit AA, Ashour HMA, Abdel Ghany YS, Bekhit AEA, Baraka AM (2008) Synthesis and biological evaluation of some thiazolyl and thiadiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial agents. Eur J Med Chem 43:456–463. doi:10.1016/j.ejmech.2007.03.030
Ozdemir Z, Kandilici HB, Gumusel B, Calis U, Bilgin AA (2007) Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives. Eur J Med Chem 42:373–379. doi:10.1016/j.ejmech.2006.09.006
Odell LR, Nilsson M, Gising J, Lagerlund O, Muthas D, Nordqvist A, Karlen A, Larhed A (2009) Functionalized 3-amino-imidazo[1,2-\(a\)]pyridines: a novel class of drug-like mycobacterium tuberculosis glutamine synthetase inhibitors. Bioorg Med Chem Lett 19:4790–4793. doi:10.1016/j.bmcl.2009.06.045
Guchhait SK, Maadan C (2009) An efficient, regioselective, versatile synthesis of N-Fused 2-and 3-Aminoimidazoles via Ugi-Type multicomponent reaction mediated by zirconium (IV) chloride in polyethylene Glycol-400. Synlett 4:628–632. doi:10.1055/s-0028-1087915
Rousseau AL, Matlaba P, Parkinson CJ (2007) Multicomponent synthesis of imidazo [1, 2-\(a\)] pyridines using catalytic zinc chloride. Tetrahedron Lett 48:4079–4082. doi:10.1016/j.tetlet.2007.04.008
Pereshivko OP, Peshkov VA, Ermolat’ev DS, Van der Eycken E (2013) Fast assembly of 1H-imidazo[1,2-\(a\)]imidazol-5-amines via Groebke–Blackburn–Bienaymé reaction with 2-aminoimidazoles. Synlett 24:351–354. doi:10.1055/s-0032-1317986
Che C, Xiang J, Wang G-X, Fathi R, Quan J-M, Yang Z (2007) One-pot synthesis of quinoline-based tetracycles by a tandem three-component reaction. J Comb Chem 9:982–989. doi:10.1021/cc070058a
Blackburn C (1998) A three-component solid-phase synthesis of 3-aminoimidazo [l,2-\(a\)]azines. Tetrahedron Lett 39:5469–5472. doi:10.1016/S0040-4039(98)01113-7
Salunke DB, Yoo E, Shukla NM, Balakrishna R, Malladi SS, Serafin KJ, Day VW, Wang X, David SA (2012) Structure-activity relationships in human toll-like receptor 8-active 2,3-diaminofuro[2,3-\(c\)]pyridines. J Med Chem 55:8137–8151. doi:10.1021/jm3000533
Abdel-Wahab BF, Khidre RE, Farahat AA (2011) Pyrazole-3(4)-carbaldehyde: synthesis, reactions and biological activity ARKIVOC i:196–245. doi:10.3998/ark.5550190.0012.103
Shaaban S, Abdel-Wahab BF (2016) Groebke–Blackburn–Bienaymé multicomponent reaction emerging chemistry for drug discovery. Mol Divers 20:233–254. doi:10.1007/s11030-015-9602-6
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R. S. and A. A. thank Manipal University Jaipur for seed money grant. S. S. thanks MUJ for teaching assistantship. Material Research Center, MNIT, Jaipur is also thanked for spectral analysis of synthesized compounds.
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Swami, S., Agarwala, A. & Shrivastava, R. Indium triflate promoted one-pot multicomponent synthesis of structurally diverse 3-amino-imidazo[1,2-a]pyridines. Mol Divers 21, 81–88 (2017). https://doi.org/10.1007/s11030-016-9699-2
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DOI: https://doi.org/10.1007/s11030-016-9699-2