Reductive Condensation of a Nitro Group with Carboxylic Acids Promoted by Phosphorus(III) Compounds: A Short Route to 5H-Dibenzo[b,e][1,4]diazepin-11(10H)-ones

Abstract

Tributyl- or triphenylphosphine promotes a one-pot, three-step method for the synthesis of differently substituted dibenzodiazepinones from N-aryl-2-nitroanilines. Pyridine analogues and the corresponding thiazepinones can also be formed using this method. The process involves deoxygenation of the nitro group, then formation of an iminophosphorane intermediate and its intramolecular condensation with a carboxyl group placed in the N-aryl group. The role of the carboxyl group in the formation of the iminophosphorane and the mode of cyclization are discussed.

Key words

cyclocondensation - reduction - nitro compounds - dibenzodiazepines - regioselectivity

• References

• 1 Tryniszewski M, Bujok R, Cmoch P, Gańczarczyk R, Kulszewicz-Bajer I, Wróbel Z. J. Org. Chem. 2019; 84: 2277
• 2 Joshua AV, Sharma SK, Strelkov A, Scott JR, Martin-Iverson MT, Abrams DN, Silverstone PH, McEwan AJ. B. Bioorg. Med. Chem. Lett. 2007; 17: 4066
• 3 Kalhapure RS, Patil BP, Jadhav MN, Kawle LA, Wagh SB. E-J. Chem. 2011; 8: 1747
• 4 Chen X, Choo H, Huang X.-P, Yang X, Stone O, Roth BL, Jin J. ACS Chem. Neurosci. 2015; 6: 476
• 5 Saadatjoo N, Javaheri M, Saemian N, Amini M. Radiochemistry 2016; 58: 423
• 6 Yu Y, Wu J, Lei F, Chen L, Wan W, Hai L, Guan M, Wu Y. Lett. Drug Des. Discovery 2013; 10: 369
• 7 Hunziker F, Fischer E, Schmutz J. Helv. Chim. Acta 1967; 50: 1588
• 8a Yoshino H, Ueda N, Niijma J, Haneda T, Kotake Y, Yoshimatsu K, Watanabe T, Nagasu T, Tsukahara N. WO 9503279, 1995 Chem. Abstr. 1995, 122, 314588
• 8b Takahashi Y, Hirokawa T, Watanabe M, Fujita S, Ogura Y, Enomoto M, Kuwahara S. Tetrahedron Lett. 2015; 56: 5670 ; and references cited therein
• 9 Kumar CP, Reddy TS, Mainkar PS, Bansal V, Shukla R, Chandrasekhar S, Hügel HM. Eur. J. Med. Chem. 2016; 108: 674
• 10 Lehner H, Gauch R, Michaelis W. Arzneim.-Forsch. 1967; 17: 185
• 11 Charan RD, Schlingmann G, Janso J, Bernan V, Feng X, Carter GT. J. Nat. Prod. 2004; 67: 1431
• 12 Hunziker F, Lauener H, Schmutz H. Arzneim.-Forsch. 1963; 13: 324
• 13a Giachetti A, Giraldo E, Ladinsky H, Montagna E. Br. J. Pharmacol. 1986; 89: 83
• 13b Tahtaoui C, Parrot I, Klotz P, Guillier F, Galzi J.-L, Hibert M, Ilien B. J. Med. Chem. 2004; 47: 4300
• 13c Holzgrabe U, Heller E. Tetrahedron 2003; 59: 781
• 14a Hasvold LA, Wang L, Przytulińska M, Xiao Z, Chen Z, Gu W.-Z, Merta PJ, Xue J, Kovar P, Zhang H, Park C, Sowin TJ, Rosenberg SH, Lin N.-H. Bioorg. Med. Chem. Lett. 2008; 18: 2311
• 14b Wang L, Sullivan GM, Hexamer LA, Hasvold LA, Thalji R, Przytulinska M, Tao ZF, Li G, Chen Z, Xiao Z, Gu WZ, Xue J, Bui MH, Merta P, Kovar P, Bouska JJ, Zhang H, Park C, Stewart KD, Sham HL, Sowin TJ, Rosenberg SH, Lin NH. J. Med. Chem. 2007; 50: 4162
• 15 Tsvelikhovsky D, Buchwald SL. J. Am. Chem. Soc. 2011; 133: 14228
• 16 Beccalli EM, Broggini G, Paladino G, Zoni C. Tetrahedron 2005; 61: 61
• 17 Majumdar KC, Sintu G. Synlett 2011; 1881
• 18a Laha JK, Manral N, Hunjan MK. New J. Chem. 2019; 43: 7339
• 18b Li Y, Zhan C, Yang B, Cao X, Ma C. Synthesis 2013; 45: 111
• 19a Giani RP, Borsa M, Parini E, Tonon GC. Synthesis 1985; 550
• 19b Levy O, Erez M, Varon D, Keinan E. Bioorg. Med. Chem. Lett. 2001; 11: 2921
• 19c Keller M, Tränkle C, She X, Pegoli A, Bernhardt G, Buschauer A, Read RW. Bioorg. Med. Chem. 2015; 23: 3970
• 20a Garcia J, Urpí F, Vilarrasa J. Tetrahedron Lett. 1984; 25: 4841
• 20b Urpí F, Vilarrasa J. Tetrahedron Lett. 1986; 27: 4623
• 20c Kovács L, Õsz E, Domokos V, Holzer W, Györgydeák Z. Tetrahedron 2001; 57: 4609
• 20d Sathishkumar M, Shanmugavelan P, Nagarajan S, Maheswari M, Dinesh M, Ponnuswamy M. Tetrahedron Lett. 2011; 52: 2830
• 21a Łukasik E, Wróbel Z. Synlett 2014; 25: 217
• 21b Łukasik E, Wróbel Z. Heteroat. Chem. 2016; 27: 372
• 22 Cadogan JI. G. Q. Rev., Chem. Soc. 1968; 22: 222
• 23a Dushek J, Vasella A. Helv. Chim. Acta 2011; 94: 977
• 23b Maki Y, Hosokami T, Suzuki M. Tetrahedron Lett. 1971; 3509
• 24 A structure analogous to compound 3 was postulated by Cadogan as an intermediate in the deoxygenation of some nitroarenes by phosphorus(III) compounds; see: Cadogan JI. G, Kulik S. J. Chem. Soc. C 1971; 2621
• 25 Wróbel Z, Kwast A. Synthesis 2010; 3865
• 26 Hargrave KD, Proudfoot JR, Grozinger KG, Cullen E, Kapadia SR, Patel UR, Fuchs VU, Mauldin SC, Vitous J, Behnke ML, Klunder JM, Pal K, Skiles JW, McNeil DW, Rose JM, Chow GC, Skoog MT, Wu JC, Schmidt G, Engel WW, Eberlein WG, Saboe TD, Campbell SJ, Rosenthal AS, Adams J. J. Med. Chem. 1991; 34: 2231
• 27 Palazzo S, Giannola LH, Caronna S. J. Heterocycl. Chem. 1974; 11: 839