10.24.4 Product Subclass 4: Pyrazino[1,2-a]indoles and Related Benzo-Fused Ring Systems

Abstract

The synthesis of pyrazino[1,2-a]indoles and related indolo[1,2-a]quinoxalines and pyrido[2′,1′:3,4]pyrazino[1,2-a]indol-5-ium salts are reviewed in this chapter. The most common routes to pyrazino[1,2-a]indoles involve cyclization of indole derivatives containing a formyl, keto, ester, or nitrile function at the 2-position. Indolo[1,2-a]quinoxalines are most readily accessed via cyclization of 1-(aryl)-1H-indoles, where the aryl group is substituted at the 2-position by either amino, iodo, or nitro functionality.

Key words

pyrazino[1,2-a]indoles - indolo[1,2-a]quinoxalines - pyrido[2′,1′:3,4]pyrazino[1,2-a]indol-5-ium salts - annulation - cyclization

• 1 Youssif BGM, Abdelrahman MH, Abdelazeem AH, Abdelgawad MA, Ibrahim HM, Salem OIA, Mohamed MFA, Treambleau L, Bukhari SNA. Eur. J. Med. Chem. 2018; 146: 260

• 2 Lin P.-T, Salunke DB, Chen L.-H, Sun C.-M. Org. Biomol. Chem. 2011; 9: 2925

• 3 Xu H, Fan L.-L. Eur. J. Med. Chem. 2011; 46: 1919

• 4 Trawczyński A, Telega M, Wróbel Z. Synlett 2015; 26: 1352

• 5 Wróbel Z, Kwast A. Synthesis 2010; 3865

• 6 Toche R, Chavan S, Janrao R. Monatsh. Chem. 2014; 145: 1507

• 7 Abbiati G, Arcadi A, Bellinazzi A, Beccalli E, Rossi E, Zanzola S. J. Org. Chem. 2005; 70: 4088

• 8 Sari O, Seybek AF, Kaya S, Menges N, Erdem SS, Balci M. Eur. J. Org. Chem. 2019; 5261

• 9 Bi H.-Y, Du M, Pan C.-X, Xiao Y, Su G.-F, Mo D.-L. J. Org. Chem. 2019; 84: 9859

• 10 Guven S, Ozer MS, Kaya S, Menges N, Balci M. Org. Lett. 2015; 17: 2660

• 11 Nayak M, Pandey G, Batra S. Tetrahedron 2011; 67: 7563

• 12 Reeves JT, Fandrick DR, Tan Z, Song JJ, Lee H, Yee NK, Senanayake CH. J. Org. Chem. 2010; 75: 992

• 13 Yuan Q, Ma D. J. Org. Chem. 2008; 73: 5159

• 14 Bentley R, Stevens TS, Thompson M. J. Chem. Soc. C 1970; 791

• 15 Sharma A, Singh M, Rai NN, Sawant D. Beilstein J. Org. Chem. 2013; 9: 1235

• 16 Verma AK, Jha RR, Sankar VK, Aggarwal T, Singh RP, Chandra R. Eur. J. Org. Chem. 2011; 6998

• 17 Agarwal PK, Sawant D, Sharma S, Kundu B. Eur. J. Org. Chem. 2009; 292

• 18 Jiang G, Wang S, Zhang J, Yu J, Zhang Z, Ji F. Adv. Synth. Catal. 2019; 361: 1798

• 19 Liu H, Duan T, Zhang Z, Xie C, Ma C. Org. Lett. 2015; 17: 2932

• 20 Liu H, Zhou F, Luo W, Chen Y, Zhang C, Ma C. Org. Biomol. Chem. 2017; 15: 7157

• 21 Zhang Z, Xie C, Tan X, Song G, Wen L, Gao H, Ma C. Org. Chem. Front. 2015; 2: 942

• 22 Sridevi B, Kandimalla SR, Reddy BVS. Eur. J. Org. Chem. 2019; 6800

• 23 Xie C, Zhang Z, Li D, Gong J, Han X, Liu X, Ma C. J. Org. Chem. 2017; 82: 3491

• 24 Xie C, Feng L, Li W, Ma X, Ma X, Liu Y, Ma C. Org. Biomol. Chem. 2016; 14: 8529

• 25 Samala S, Arigela RK, Kant R, Kundu B. J. Org. Chem. 2014; 79: 2491

• 26 Beach MJ, Hope R, Klaubert DH, Russell RK. Synth. Commun. 1995; 25: 2165

• 27 Joseph MS, Basanagoudar LD. Synth. Commun. 2003; 33: 851

• 28 Romagnoli R, Baraldi PG, Carrion MD, Cruz-Lopez O, Cara CL, Preti D, Tabrizi MA, Balzarini J, Hamel E, Fabbri E, Gambari R. Lett. Drug Des. Discovery 2009; 6: 298

• 29 Festa AA, Zalte RR, Golantsov NE, Varlamov AV, Van der Eycken EV, Voskressensky LG. J. Org. Chem. 2018; 83: 9305

• 30 Festa AA, Golantsov NE, Storozhenko OA, Shumsky AN, Varlamov AV, Voskressensky LG. Synlett 2018; 29: 898

• 31 Ohsawa A, Kawaguchi T, Igeta H. Synthesis 1983; 1037

• 32 Atfah A, Abu-Shuheil MY, Hill J. Tetrahedron 1990; 46: 6483