A Rapid One-Pot Ugi Reaction Based Route to Novel Imidazole-Fused Benzodiazepinones

Abstract

A short and efficient synthetic approach has been developed for the synthesis of a variety of imidazole-fused benzodiazepinones. It is based on a Ugi multicomponent reaction strategy and uses various isocyanides to generate the key intermediates for a Mumm rearrangement process. The method is suitable for rapid syntheses of fused azaheterocycles of pharmacological interest.

Key words

multicomponent reactions - heterocycles - fused-ring systems - isocyanides - imidazoles - rearrangements

• References

• 1a Bienaymé H, Hulme C, Oddon G, Schmitt P. Chem. Eur. J. 2000; 6: 3321
• 1b Simon C, Constantieux T, Rodriguez J. Eur. J. Org. Chem. 2004; 4957
• 1c Multicomponent Reactions . Zhu J, Bienaymé H. Wiley-VCH; Weinheim: 2005
• 1d Liang B, Wang X, Wang J.-X, Du Z. Tetrahedron 2007; 63: 1981
• 1e Syamala M. Org. Prep. Proced. Int. 2009; 41: 1
• 1f Sun J, Xia E.-Y, Zhang L.-L, Yan C.-G. Eur. J. Org. Chem. 2009; 5247
• 1g Gérard S, Renzetti A, Lefevre B, Fontana A, de Maria P, Sapi J. Tetrahedron 2010; 66: 3065
• 1h Song W, Lu W, Wang J, Lu P, Wang Y. J. Org. Chem. 2010; 75: 3481
• 2 Bohacek RS, McMartin C, Guida WC. Med. Res. Rev. 1996; 16: 3
• 3 Dömling A. Curr. Opin. Chem. Biol. 2000; 4: 318
• 4a Dömling A, Ugi I. Angew. Chem. Int. Ed. 2000; 39: 3168
• 4b Nair V, Rajesh C, Vinod AU, Bindu S, Sreekanth AR, Mathen JS, Balagopal L. Acc. Chem. Res. 2003; 36: 899
• 4c Li J, Liu Y, Li C, Jia X. Tetrahedron Lett. 2009; 50: 6502
• 4d García-González MC, González-Zamora E, Santillan R, Domínguez O, Méndez-Stivalet JM, Farfán N. Tetrahedron 2009; 65: 5337
• 4e Adib M, Mahdavi M, Bagherzadeh S, Zhu L.-G, Rahimi-Nasrabadi M. Tetrahedron Lett. 2010; 51: 27
• 4f Mitra S, Hota SK, Chattopadhyay P. Synthesis 2010; 3899
• 5a Dömling A. Chem. Rev. 2006; 106: 17
• 5b Isonitrile Chemistry . Ugi I. Academic Press; New York: 1971
• 6a Ireland SM, Tye H, Whittaker M. Tetrahedron Lett. 2003; 44: 4369
• 6b Schwerkoske J, Masquelin T, Perun T, Hulme C. Tetrahedron Lett. 2005; 46: 8355
• 6c Ramazani A, Mahyari AT, Rouhani M, Rezaei A. Tetrahedron Lett. 2009; 50: 5625
• 6d Guchhait SK, Madaan C. Org. Biomol. Chem. 2010; 8, 3631
• 6e De Moliner F, Hulme C. Org. Lett. 2012; 14: 1354
• 6f Kulsi G, Ghorai A, Chattopadhyay P. Tetrahedron Lett. 2012; 53: 3619
• 7a Ugi I, Meyer R, Fetzer U, Steinbrückner C. Angew. Chem. 1959; 71: 386
• 7b Ugi I, Steinbrückner C. Angew. Chem. 1960; 72: 267
• 7c Ugi I, Steinbrückner C. Chem. Ber. 1961; 94: 2802
• 7d De Silva RA, Santra S, Andreana PR. Org. Lett. 2008; 10: 4541
• 7e Faggi C, García-Valverde M, Marcaccini S, Menchi G. Org. Lett. 2010; 12: 788
• 8a Passerini M. Gazz. Chim. Ital. 1921; 51: 126
• 8b Passerini M. Gazz. Chim. Ital. 1921; 51: 181.
• 9a De Clercq E. Farmaco 2001; 56: 3
• 9b De Clercq E. Farmaco 1999; 54: 26
• 10 Watjen F, Baker R, Engelstoff M, Herbert R, MacLeod A, Knight A, Merchant K, Moseley J, Saunders J, Swain CJ, Wong E, Springer JP. J. Med. Chem. 1989; 32: 2282
• 11 Anzini M, Braile C, Valenti S, Cappelli A, Vomero S, Marinelli L, Limongelli V, Novellino E, Betti L, Giannaccini G, Lucacchini A, Ghelardini C, Norcini M, Makovec F, Giorgi G, Fryer RI. J. Med. Chem. 2008; 51: 4730
• 12 Leimgruber W, Stefanović V, Schenker F, Karr A, Berger J. J. Am. Chem. Soc. 1965; 87: 5791.
• 13 Hamann LG, Ding CZ, Miller AV, Madsen CS, Wang P, Stein PD, Pudzianowski AT, Green DW, Monshizadegan H, Atwal KS. Bioorg. Med. Chem. Lett. 2004; 14: 1031
• 14 Tashma Z, Raveh L, Liani H, Alkalay D, Givoni S, Kapon J, Cohen G, Alcalay M, Grauer E. J. Appl. Toxicol. 2001; 21: S115
• 15 Liu R, Hu RJ, Zhang P, Skolnick P, Cook JM. J. Med. Chem. 1996; 39: 1928
• 16 Albright JD, Feich MF, Delos Santos EG, Dusza JP, Sum F.-W, Venkatesan AM, Coupet J, Chan PS, Ru X, Mazandarani H, Bailey T. J. Med. Chem. 1998; 41: 2442
• 17a Selnick HG, Liverton NJ, Baldwin JJ, Butcher JW, Claremon DA, Elliott JM, Freidinger RM, King SA, Libby BE, McIntyre CJ, Pribush DA, Remy DC, Smith GR, Tebben AJ, Jurkiewicz NK, Lynch JJ, Salata JJ, Sanguinetti MC, Siegl PK. S, Slaughter DE, Vyas K. J. Med. Chem. 1997; 40: 3865
• 17b Olkkola KT, Ahonen J. Handb. Exp. Pharmacol. 2008; 182: 335
• 18 Castro JL, Broughton HB, Russell MG. N, Rathbone D, Watt AP, Ball RG, Chapman KL, Patel S, Smith AJ, Marshall GR, Matassa VG. J. Med. Chem. 1987; 40: 2491
• 19 Nguyen HH, Palazzo TA, Kurth MJ. Org. Lett. 2013; 15: 4492
• 20a Adhikary ND, Chattopadhyay P. Eur. J. Org. Chem. 2010; 1754
• 20b Mitra S, Darira H, Chattopadhyay P. Synthesis 2013; 45: 85
• 21 Mandrioli R, Mercolini L, Raggi MA. Curr. Drug Metab. 2008; 9: 827
• 22 El Kaim L, Grimaud L. Tetrahedron 2009; 65: 2153