10.24.1 Product Subclass 1: Pyrido[1,2-a]indoles and Related Benzo-Fused Ring Systems

Abstract

This review describes methods for the synthesis of pyrido[1,2-a]indoles, as well as the related benzo-fused ring systems indolo[1,2-a]quinolines, indolo[1,2-b]isoquinolines, indolo[2,1-a]isoquinolines, and indolo[1,2-f]phenanthridines. The most common routes to access these ring systems involve a variety of transition-metal-catalyzed cyclizations, but alternative approaches are also covered.

Schlüsselwörter

pyrido[1,2-a]indoles - indolo[1,2-a]quinolines - indolo[1,2-b]isoquinolines - indolo[2,1-a]isoquinolines - indolo[1,2-f]phenanthridines - cyclization

• 1 Sun H, Wang C, Yang Y.-F, Chen P, Wu Y.-D, Zhang Xi, Huang Y. J. Org. Chem. 2014; 79: 11 863

• 2 Borthakur S, Sarma B, Gogoi S. Org. Lett. 2019; 21: 7878

• 3 Kraus GA, Beasley J. Tetrahedron Lett. 2013; 54: 5597

• 4 Gao J, Shao Y, Zhu J, Zhu J, Mao H, Wang X, Lv X. J. Org. Chem. 2014; 79: 9000

• 5 Gao J, Xu B, Zhu J, Shao Y, Chen L, Zhu J, Wang X, Lv X. ARKIVOC 2016; 1

• 6 Ngo TN, Ehlers P, Dang TT, Villinger A, Langer P. Org. Biomol. Chem. 2015; 13: 3321

• 7 Samala S, Pallavi P, Kumar R, Arigela RK, Singh G, Ampapathi RS, Priya A, Datta S, Patra A, Kundu B. Chem.–Eur. J. 2014; 20: 14 344

• 8 Zhu H, Stöckigt J, Yu Y, Zou H. Org. Lett. 2011; 13: 2792

• 9 Takeda D, Hirano K, Satoh T, Miura M. Heterocycles 2012; 86: 487

• 10 Yan L, Zhao D, Lan J, Cheng Y, Guo Q, Li X, Wu N, You J. Org. Biomol. Chem. 2013; 11: 7966

• 11 Lee HK, Dao PDQ, Kim Y.-s, Cho CS. Synthesis 2018; 50: 3243

• 12 Morimoto K, Hirano K, Satoh T, Miura M. Org. Lett. 2010; 12: 2068

• 13 Ackermann L, Wang L, Lygin AV. Chem. Sci. 2012; 3: 177

• 14 Kobayashi K, Ezaki K, Hanioka D, Nozawa I. Helv. Chim. Acta 2015; 98: 179

• 15 Xia Y.-Q, Dong L. Org. Lett. 2017; 19: 2258

• 16 Chen G, Zhang X, Jia R, Li B, Fan X. Adv. Synth. Catal. 2018; 360: 3781

• 17 Outlaw VK, Zhou J, Bragg AE, Townsend CA. RSC Adv. 2016; 6: 61 249

• 18 Thanetchaiyakup A, Rattanarat H, Chuanopparat N, Ngernmeesri P. Tetrahedron Lett. 2018; 59: 1014

• 19 Jiang Z.-q, Miao D.-z, Tong Y, Pan Q, Li X.-t, Hu R.-h, Han S.-q. Synthesis 2015; 47: 1913

• 20 Dawande SG, Lad BS, Prajapati S, Katukojvala S. Org. Biomol. Chem. 2016; 14: 5569

• 21 Kong L, Yao Q, Wang M, Sun R, Li Y. ChemistrySelect 2018; 3: 456

• 22 Verma AK, Kesharwani T, Singh J, Tandon V, Larock RC. Angew. Chem. Int. Ed. 2009; 48: 1138

• 23 Sun L.-L, Liao Z.-Y, Tang R.-Y, Deng C.-L, Zhang X.-G. J. Org. Chem. 2012; 77: 2850

• 24 Lötter ANC, Pathak R, Sello TS, Fernandes MA, van Otterlo WAL, de Koning CB. Tetrahedron 2007; 63: 2263

• 25 Xie C, Zhang Y, Huang Z, Xu P. J. Org. Chem. 2007; 72: 5431

• 26 Shukla SP, Tiwari RK, Verma AK. J. Org. Chem. 2012; 77: 10 382

• 27 Hulcoop DG, Lautens M. Org. Lett. 2007; 9: 1761

• 28 Liu X, Li X, Liu H, Guo Q, Lan J, Wang R, You J. Org. Lett. 2015; 17: 2936

• 29 Florentino L, Aznar F, Valdés C. Chem.–Eur. J. 2013; 19: 10 506

• 30 Chai DI, Lautens M. J. Org. Chem. 2009; 74: 3054

• 31 Ye S, Liu J, Wu J. Chem. Commun. (Cambridge) 2012; 48: 5028

• 32 Verma AK, Shukla SP, Singh J, Rustagi V. J. Org. Chem. 2011; 76: 5670

• 33 Sun K, Chen X.-L, Zhang Y.-L, Li K, Huang X.-Q, Peng Y.-Y, Qu L.-B, Yu B. Chem. Commun. (Cambridge) 2019; 55: 12 615

• 34 Kiselyov AS. Tetrahedron 2006; 62: 543

• 35 Mandal T, Chakraborti G, Karmakar S, Dash J. Org. Lett. 2018; 20: 4759

• 36 Kotha S, Aswar VR, Singhal G. Tetrahedron 2017; 73: 6436

• 37 Biswas S, Singh V, Batra S. Tetrahedron 2010; 66: 7781

• 38 Chesnokov GA, Ageshina AA, Topchiy MA, Nechaev MS, Asachenko AF. Eur. J. Org. Chem. 2019; 4844

• 39 Rogness DC, Markina NA, Waldo JP, Larock RC. J. Org. Chem. 2012; 77: 2743

• 40 Dalton LK, Teitei T. Aust. J. Chem. 1969; 22: 1525

• 41 Ohsawa A, Kawaguchi T, Igeta H. J. Org. Chem. 1982; 47: 3497

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

• 43 Karthikeyan I, Sekar G. Eur. J. Org. Chem. 2014; 8055

• 44 Karthikeyan I, Arunprasath D, Sekar G. Chem. Commun. (Cambridge) 2015; 51: 1701

• 45 Chuentragool P, Li Z, Randle K, Mahchi F, Ochir I, Assaf S, Gevorgyan V. J. Organomet. Chem. 2018; 867: 273

• 46 Wei X, Qu B, Zeng X, Savoie J, Fandrick KR, Desrosiers J.-N, Tcyrulnikov S, Marsini MA, Buono FG, Li Z, Yang B.-S, Tang W, Haddad N, Gutierrez O, Wang J, Lee H, Ma S, Campbell S, Lorenz JC, Eckhardt M, Himmelsbach F, Peters S, Patel ND, Tan Z, Yee NK, Song JJ, Roschangar F, Kozlowski MC, Senanayake CH. J. Am. Chem. Soc. 2016; 138: 15 473

• 47 Nikonov IL, Kopchuk DS, Kovalev IS, Zyryanov GV, Khasanov AF, Slepukhin PA, Rusinov VL, Chupakhin ON. Tetrahedron Lett. 2013; 54: 6427

• 48 Kozhevnikov VN, Kozhevnikov DN, Shabunina OV, Rusinov VL, Chupakhin ON. Tetrahedron Lett. 2005; 46: 1791

• 49 Labelle M, Montalbetti CAGN, Mears RJ, Vile J, Gelman DM, Gai X, Barker OR, Deboves HJC, East SP, Boesen T. WO 2012 007 007, 2012

• 50 Soldatenkov AT, Ntaganda Z, Soldatova SA, Alarkon KAR, Anisimov BN, Golovtsov NI. Chem. Heterocycl. Compd. (Engl. Transl.) 1999; 35: 699

• 51 Ntaganda Zh, Soldatova SA, Alarkon HAR, Anisimov BN, Soldatenkov AT. Khim. Geterotsikl. Soedin. 1994; 83

• 52 Jones G, Stanforth SP. Org. React. (N. Y.) 1997; 49: 33