New Efficient Synthesis of 1,4-Benzodiazepin-5-ones by Catalytic Aza-Wittig Reaction

Abstract

1,4-Benzodiazepin-5-ones were synthesized in 71–89% yields from 2-isocyanato-N-(2-oxoalkyl)benzamides via a new catalytic intramolecular aza-Wittig reaction. Starting from easily accessible phthalic anhydride and α-arylamino ketones, the corresponding 2-{[(2-oxoalkyl)amino]carbonyl}benzoic acids underwent sequential formation of the acid azide and Curtis rearrangement to give 2-isocyanato-N-(2-oxoalkyl)benzamides that were reacted directly to give the final 2,4-diaryl-3,4-dihydro-5H-1,4-benzodiazepin-5-ones and 4-aryl-2-tert-butyl-3,4-dihydro-5H-1,4-benzodiazepin-5-ones.

Key words

1,4-benzodiazepin-5-one - catalytic aza-Wittig reaction - Curtius reaction - acyl azide - isocyanate

• References

• 1a Costantino L, Barlocco D. Curr. Med. Chem. 2006; 13: 65
• 1b Garofalo A, Balconi G, Botta M, Corelli F, D’Incalci M, Fabrizi G, Fiorini I, Lamba D, Nacci V. Eur. J. Med. Chem. 1993; 28: 213
• 2a Bose DS, Idrees M, Todewale IK, Jakka NM, Rao JV. Eur. J. Med. Chem. 2012; 50: 27
• 2b Kamal A, Reddy MK, Ramaiah MJ, Rajender, Reddy JS, Srikanth YV. V, Dastagiri D, Bharathi EV, Pushpavalli SN. C. V. L, Sarma P, Pal-Bhadra M. Bioorg. Med. Chem. 2011; 19: 2565
• 2c Kamal A, Balakishan G, Ramakrishna GT, Shaik TB, Sreekanth K, Balakrishna M, Rajender, Dastagiri D, Kalivendi SV. Eur. J. Med. Chem. 2010; 45: 3870
• 2d Kamal A, Sreekanth K, Kumar PP, Shankaraiah N, Balakishan G, Ramaiah MJ, Pushpavalli SN. C. V. L, Ray P, Bhadra MP. Eur. J. Med. Chem. 2010; 45: 2173
• 3 Sobańska AW, Żydek G, Włodno P, Brzezińska E. Eur. J. Med. Chem. 2015; 89: 147
• 4 Guandalini L, Balliu M, Cellai C, Martino MV, Nebbioso A, Mercurio C, Carafa V, Bartolucci G, Dei S, Manetti D, Teodori E, Scapecchi S, Altucci L, Paoletti F, Romanelli MN. Eur. J. Med. Chem. 2013; 66: 56
• 5 Mita Y, Dodo K, Noguchi-Yachide T, Hashimoto Y, Ishikawa M. Bioorg. Med. Chem. Lett. 2013; 21: 993
• 6 Thurston DE. Molecular Aspects of Anticancer Drug-DNA Interactions. Macmillan; London: 1993: 54-88
• 7a Yar M, McGarrigle EM, Aggarwal VK. Org. Lett. 2009; 11: 257
• 7b Wang JY, Guo XF, Wang DX, Huang ZT, Wang MX. J. Org. Chem. 2008; 73: 1979
• 7c Attanasi OA, Crescentini LD, Favi G, Mantellini F, Nicolini S. J. Org. Chem. 2011; 76: 8320
• 7d Salomé C, Schmitt M, Bourguignon J.-J. Tetrahedron Lett. 2012; 53: 1033
• 7e Santilli AA, Osdene TS. J. Org. Chem. 1964; 29: 1998
• 7f Lee S.-C, Park SB. Chem. Commun. 2007; 3714
• 7g Viviano M, Milite C, Rescigno D, Castellano S, Sbardella G. RSC Adv. 2015; 5: 1268
• 8a Santagada V, Perissutti E, Fiorino F, Vivenzio B, Caliendo G. Tetrahedron Lett. 2001; 42: 2397
• 8b Basolo L, Beccalli EM, Borsini E, Broggini G, Khansaa M, Rigamonti M. Eur. J. Org. Chem. 2010; 1694
• 9a Beccalli EM, Broggini G, Paladino G, Penoni A, Zoni C. J. Org. Chem. 2004; 69: 5627
• 9b Neukom JD, Aquino AS, Wolfe JP. Org. Lett. 2011; 13: 2196
• 10a Gil C, Bräse S. Chem. Eur. J. 2005; 11: 2680
• 10b Eguchi S, Yamashita K, Matsushita Y, Kakehi A. J. Org. Chem. 1995; 60: 4006
• 11 Marcaccini S, Miliciani M, Pepino R. Tetrahedron Lett. 2005; 46: 711

For reviews, see:
• 12a Fresneda PM, Molina P. Synlett 2004; 1
• 12b Palacios F, Alonso C, Aparicio D, Rubiales G, Santos JM. Tetrahedron 2007; 63: 523
• 12c Palacios F, Aparicio D, Rubiales G, Alonso C, de los Santos JM. Curr. Org. Chem. 2009; 13: 810
• 12d Eguchi S. ARKIVOC 2005; (ii): 98 ; http://www.arkat-usa.org/home
• 12e Palacios F, Alonso C, Aparicio D, Rubiales G, de los Santos JM In Organic Azides: Synthesis and Applications . Bräse S, Banert K. John Wiley; Chichester: 2010: 437

For recent application of intramolecular aza-Wittig reaction in heterocyclic synthesis, see:
• 13a Kumar R, Ermolat’ev DS, Van der Eycken EV. J. Org. Chem. 2013; 78: 5737
• 13b Fesenko AA, Shutalev AD. Tetrahedron 2014; 70: 5398
• 13c Okamoto K, Shimbayashi T, Tamura E, Ohe K. Chem. Eur. J. 2014; 20: 1490
• 13d Akbarzadeh R, Amanpour T, Bazgir A. Tetrahedron 2014; 70: 8142
• 13e Fesenko AA, Shutalev AD. J. Org. Chem. 2013; 78: 1190
• 13f Liu Y, Liu J, Qi X, Du Y. J. Org. Chem. 2012; 77: 7108
• 14a Marsden SP, McGonagle AE, McKeever-Abbas B. Org. Lett. 2008; 10: 2589
• 14b Marsden SP In Sustainable Catalysis . Dunn PJ, Hii KK, Krische MJ, Williams MT. John Wiley; Chichester: 2013: 339

For catalytic Wittig and other reactions based on the in situ reduction of a phosphine oxide:
• 15a O’Brien CJ, Tellez JL, Nixon ZS, Kang LJ, Carter AL, Kunkel SR, Przeworski KC, Chass GA. Angew. Chem. Int. Ed. 2009; 48: 6836
• 15b O’Brien CJ, Nixon ZS, Holohan AJ, Kunkel SR, Tellez JL, Doonan BJ, Coyle EE, Lavigne F, Kang LJ, Przeworski KC. Chem. Eur. J. 2013; 19: 15281
• 15c Coyle EE, Doonan BJ, Holohan AJ, Walsh KA, Lavigne F, Krenske EH, O’Brien CJ. Angew. Chem. Int. Ed. 2014; 53: 12907
• 15d O’Brien CJ, Lavigne F, Coyle EE, Holohan AJ, Doonan BJ. Chem. Eur. J. 2013; 19: 5854
• 15e Werner T, Hoffmann M, Deshmukh S. Eur. J. Org. Chem. 2014; 6630
• 15f Werner T, Hoffmann M, Deshmukh S. Eur. J. Org. Chem. 2014; 6873
• 15g Kosal AD, Wilson EE, Ashfeld BL. Angew. Chem. Int. Ed. 2012; 51: 12036
• 15h Denton RM, An J, Adeniran B. Chem. Commun. 2010; 46: 3025
• 15i Denton RM, Tang X, Przeslak A. Org. Lett. 2010; 12: 4678
• 15j Denton RM, An J, Lindovska P, Lewis W. Tetrahedron 2012; 68: 2899
• 15k An J, Tang X, Moore J, Lewis W, Denton RM. Tetrahedron 2013; 69: 8769
• 15l Yu T.-Y, Wang Y, Xu P.-F. Chem. Eur. J. 2014; 20: 98
• 15m Zhao W, Yan PK, Radosevich AT. J. Am. Chem. Soc. 2015; 137: 616
• 15n Dunn N, Ha M, Radosevich AT. J. Am. Chem. Soc. 2012; 134: 11330

For catalytic aza-Wittig reaction based on the in situ reduction of a phosphine oxide:
• 16a van Kalkeren HA, te Grotenhuis C, Haasjes FS, Hommersom CA, Rutjes FP. J. T, van Delft FL. Eur. J. Org. Chem. 2013; 7059
• 16b Wang L, Wang Y, Chen M, Ding MW. Adv. Synth. Catal. 2014; 356: 1098
• 16c Bel Abed H, Mammoliti O, Bande O, van Lommen G, Herdewijn P. Org. Biomol. Chem. 2014; 12: 7159
• 17a Xie H, Yuan D, Ding MW. J. Org. Chem. 2012; 77: 2954
• 17b Nie YB, Wang L, Ding MW. J. Org. Chem. 2012; 77: 696
• 17c Wang L, Ren ZL, Chen M, Ding MW. Synlett 2014; 25: 721
• 17d Wang Y, Chen M, Ding MW. Tetrahedron 2013; 69: 9056
• 17e Yuan D, Kong HH, Ding MW. Tetrahedron 2015; 71: 419
• 17f Wang Y, Xie H, Pan YR, Ding MW. Synthesis 2014; 46: 336
• 18 Sato I, Morihira K, Inami H, Kubota H, Morokata T, Suzuki K, Iura Y, Nitta A, Imaoka T, Takahashi T, Takeuchi M, Ohta M, Tsukamoto S. Bioorg. Med. Chem. 2008; 16: 8607
• 19 Congiu C, Cocco MT, Onnis V. Bioorg. Med. Chem. Lett. 2008; 18: 989
• 20 Hall CR, Smith DJ. H, Watts P. J. Chem. Soc., Perkin Trans. 2 1977; 1379
• 21 Nayak M, Pandey G, Batra S. Tetrahedron 2011; 67: 7563