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DOI: 10.1055/s-0037-1610349
Recent Advances in the Synthesis of Unsymmetrical Bisindolylmethane Derivatives
Financial support from the University of Camerino is gratefully acknowledged.Publication History
Received: 20 September 2018
Accepted after revision: 05 November 2018
Publication Date:
13 December 2018 (online)
Abstract
This review article summarizes the fundamental synthetic procedures aimed at the preparation of unsymmetrical bisindolylmethanes that have appeared in the literature since 2010. To this goal, reactive electrophilic indole-containing intermediates are mostly generated from indolylmethanols, indolylmethanamines, and indolylmethanthio derivatives and then made to react with simple or functionalized indoles. The asymmetric synthesis of bisindolylmethanes can be also achieved under chiral-catalyzed conditions.
1 Introduction
2 Direct Three-Component Coupling
3 Reaction of Indolylmethanols
4 Reaction of Indolylmethanamine Derivatives
5 Reaction of 3-Vinylindoles
6 Reaction of indolylmethanthio Derivatives
7 Bisindolylmethanes by Ring Closure of Alkyne Derivatives
8 Miscellaneous Methods
9 Conclusion
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References
- 1 Shiri M, Zolfigol MA, Kruger HG, Tanbakouchian Z. Chem. Rev. 2010; 110: 2250
- 2 Shiri M. Chem. Rev. 2012; 112: 3508
- 3 Gupta L, Talwar A, Chauhan PM. S. Curr. Med. Chem. 2007; 14: 1789
- 4 Safe S, Papineni S, Chintharlapalli S. Cancer Lett. 2008; 269: 326
- 5 Kramer H.-J, Podobinska M, Bartsch A, Battmann A, Thoma W, Bernd A, Kummer W, Irlinger B, Steglich W, Mayser P. ChemBioChem 2005; 6: 860
- 6a Queiroz MM. F, Queiroz EF, Zeraik ML, Ebrahimi SN, Marcourt L, Cuendet M, Castro-Gamboa I, Hamburger M, Bolzani VS, Wolfender J.-L. J. Nat. Prod. 2014; 77: 650
- 6b Contractor R, Samudio IJ, Estrov Z, Harris D, McCubrey JA, Safe SH, Andreeff M, Konopleva M. Cancer Res. 2005; 65: 2890
- 7a Palmieri A, Petrini M, Shaikh RR. Org. Biomol. Chem. 2010; 8: 1259
- 7b Palmieri A, Petrini M. Chem. Rec. 2016; 16: 1353
- 7c Lancianesi S, Palmieri A, Petrini M. Chem. Rev. 2014; 114: 7108
- 8 Deb ML, Deka B, Saikia PJ, Baruah PK. Tetrahedron Lett. 2017; 58: 1999
- 9 Xiao J, Wen H, Wang L, Xu L, Hao Z, Shao C.-L, Wang C.-Y. Green Chem. 2016; 18: 1032
- 10 Wen H, Wang L, Xu L, Hao Z, Shao C.-L, Wang C.-Y, Xiao J. Adv. Synth. Catal. 2015; 357: 4023
- 11 Zou Y, Chen C, Chen X, Zhang X, Rao W. Eur. J. Org. Chem. 2017; 2266
- 12 Sasaki S, Ikekame Y, Tanayama M, Yamauchi T, Higashiyama K. Synlett 2012; 23: 2699
- 13 Suárez A, Martínez F, Sanz R. Org. Biomol. Chem. 2016; 14: 11212
- 14 Shang H, Hao F.-Y, Pan L, Chen H, Cheng M.-S. Heterocycles 2011; 83: 1757
- 15 Li R.-J, Zhou Y, Zheng Y, Hai L, Wu Y. Tetrahedron Lett. 2016; 57: 2829
- 16 Chinta BS, Baire B. Tetrahedron Lett. 2016; 57: 5381
- 17 Inamdar SM, Gonnade RG, Patil NT. Org. Biomol. Chem. 2017; 15: 863
- 18 For a recent review on indole alkenylations see: Petrini M. Chem.–Eur. J. 2017; 23: 16115
- 19 He Y.-Y, Sun X.-X, Li G.-H, Mei G.-J, Shi F. J. Org. Chem. 2017; 82: 2462
- 20 Maji R, Mallojjala SC, Wheeler SE. Chem. Soc. Rev. 2018; 47: 1142
- 21 Zhuo M.-H, Jiang Y.-J, Fan Y.-S, Gao Y, Liu S, Zhang S. Org. Lett. 2014; 16: 1096
- 22 Zhuo M.-H, Liu G.-F, Song S.-L, An D, Gao J, Zheng L, Zhang S. Adv. Synth. Catal. 2016; 358: 808
- 23 Sun X.-X, Du B.-X, Zhang H.-H, Ji L, Shi F. ChemCatChem 2015; 7: 1211
- 24 Qi S, Liu C.-Y, Ding J.-Y, Han F.-S. Chem. Commun. 2014; 50: 8605
- 25 Gong Y.-X, Wu Q, Zhang H.-H, Zhu Q.-N, Shi F. Org. Biomol. Chem. 2015; 13: 7393
- 26 Liu J.-X, Zhu Z.-Q, Yu L, Du B.-X, Mei G.-J, Shi F. Synthesis 2018; 50: 3436
- 27 Yue C, Na F, Fang X, Cao Y, Antilla JC. Angew. Chem. Int. Ed. 2018; 57: 11004
- 28 Semenov BB, Granik VG. Pharm. Chem. J. 2004; 38: 287
- 29 Deb ML, Das C, Deka B, Saikikia PJ, Baruah PK. Synlett 2016; 27: 2788
- 30 Pillaiyar T, Gorska E, Schnakenburg G, Müller CE. J. Org. Chem. 2018; 83: 9902
- 31 He Q.-L, Sun F.-L, Zheng X.-J, You S.-L. Synlett 2009; 1111
- 32 Sun F.-L, Zheng X.-J, Gu Q, He Q.-L, You S.-L. Eur. J. Org. Chem. 2011; 47
- 33 Auvil TJ, So SS, Mattson AE. Angew. Chem. Int. Ed. 2013; 52: 11317
- 34 Jadhav SD, Singh A. J. Org. Chem. 2016; 81: 522
- 35 Deb ML, Borpatra PJ, Saikikia PJ, Baruah PK. Org. Biomol. Chem. 2017; 15: 1435
- 36 Li D, Wu T, Liang K, Xia C. Org. Lett. 2016; 18: 2228
- 37 Pathak TP, Osiak JG, Vaden RM, Welm BE, Sigman MS. Tetrahedron 2012; 68: 5203
- 38 Zhang Y, Zhang S.-X, Fu L.-N, Guo Q.-X. ChemCatChem 2017; 9: 3107
- 39 Palmieri A, Petrini M. J. Org. Chem. 2007; 72: 1863
- 40 Lancianesi S, Palmieri A, Petrini M. Adv. Synth. Catal. 2012; 354: 3539
- 41 Barbero M, Cadamuro S, Cauda F, Dughera S, Gervasio G, Venturello P. J. Org. Chem. 2012; 77: 4278
- 42 Barbero M, Buscaino R, Cadamuro S, Dughera S, Gualandi A, Marabello D, Cozzi PG. J. Org. Chem. 2015; 80: 4291
- 43 Abe T, Ikeda T, Itoh T, Hatae N, Toyota E, Ishikura M. Heterocycles 2014; 88: 187
- 44 Pillaiyar T, Köse M, Sylvester K, Weighardt H, Thimm D, Borges G, Förster I, von Kügelgen I, Müller C. J. Med. Chem. 2017; 60: 3636
- 45a Herraiz-Cobo J, Albericio F, Álvarez M. Adv. Heterocycl. Chem. 2015; 116: 1
- 45b Krüger K, Tillack A, Beller M. Adv. Synth. Catal. 2008; 350: 2153
- 46 Shu D, Winston-McPherson GN, Song W, Tang W. Org. Lett. 2013; 15: 4162
- 47 Winston-McPherson GN, Shu D, Tang W. Bioorg. Med. Chem. Lett. 2014; 24: 4023
- 48 Li H, Li X, Wang H.-Y, Winston-McPherson GN, Geng HJ, Guzei IA, Tang W. Chem. Commun. 2014; 50: 12293
- 49 Lu Q, Cembellín S, Greßies A, Singha S, Daniliuc CG, Glorius F. Angew. Chem. Int. Ed. 2018; 57: 1399
- 50 Deb ML, Pegu CD, Deka B, Dutta P, Kotmale AS, Baruah PK. Eur. J. Org. Chem. 2016; 3441
- 51 Armstrong EL, Grover HK, Kerr MA. J. Org. Chem. 2013; 78: 10534
- 52 Yu J.-B, Zhang Y, Jiang Z.-J, Su W.-K. J. Org. Chem. 2016; 81: 11514
For general reviews on the utilization of this type of intermediates in synthesis see: