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Synthesis 2015; 47(21): 3301-3308
DOI: 10.1055/s-0035-1560065
DOI: 10.1055/s-0035-1560065
paper
N-Arylation of Sterically Hindered NH-Nucleophiles: Copper-Mediated Syntheses of Diverse N-Arylindole-2-carboxylates
Further Information
Publication History
Received: 01 June 2015
Accepted after revision: 07 July 2015
Publication Date:
20 August 2015 (online)
Abstract
Indole-carboxylates are N-arylated with 2-bromopyridines using stoichiometric copper(II) oxide/potassium carbonate to give various N-(2-pyridyl)-substituted indole-2-carboxylates and with bromobenzenes using stoichiometric copper(I) iodide/N,N′-dimethylethylenediamine to give various N-(substituted phenyl)-substituted indole-2-carboxylates. These results expand the scope of metal-catalyzed N-arylation using heterocyclic amines with steric bulk and weak nucleophilicity.
Key words
copper - N-arylation - indoles - copper-mediated synthesis - heterocyclic amines - metal-catalyzedSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560065.
- Supporting Information
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References
- 1a Comprehensive Heterocyclic Chemistry II . Katritzky AR, Rees CW, Scriven EF. V. Elsevier; Oxford: 1996
- 1b Craig PN In Comprehensive Medicinal Chemistry . Vol. 8. Drayton CJ. Pergamon; Oxford: 1991
- 1c Cozzi P, Carganico G, Fusar D, Grossoni M, Menichincheri M, Pinciroli V, Tonani R, Vaghi F, Salvati P. J. Med. Chem. 1993; 36: 2964
- 2a Pelcman B, Olofsson K, Katkevics M, Ozola V, Suna E, Kalvins I, Trapencieris P, Katkevica D, Schaal W. WO 2006077367, 2006
- 2b Dubois L, Evanno Y, Malanda A, Maloizel C. WO 2008107544, 2008
- 2c Sinz C, Bittner A, Brady E, Candelore M, Dallas-Yang Q, Ding V, Jiang G, Lin Z, Qureshi S, Salituro G, Saperstein R, Shang J, Szalkowski D, Tota L, Vincent S, Wright M, Xu S, Yang X, Zhang B, Tata J, Kim R, Parmee ER. Bioorg. Med. Chem. Lett. 2011; 21: 7124
- 2d Olofsson K, Suna E, Pelcman B, Ozola V, Katkevics M, Kalvins I, Schaal W. WO 2005123675, 2005
- 3a Djakovitch L, Batail N, Genelot M. Molecules 2011; 16: 5241 ; http://www.mdpi.com/journal/molecules
- 3b Xu H. Mini-Rev. Org. Chem. 2009; 6: 367
- 3c Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954
- 4a Klapars A, Antilla JC, Huang X, Buchwald SL. J. Am. Chem. Soc. 2001; 123: 7727
- 4b Antilla JC, Klapars A, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 11684
- 4c Altman RA, Koval ED, Buchwald SL. J. Org. Chem. 2007; 72: 6190
- 4d Zhu L, Cheng L, Zhang Y, Xie R, You J. J. Org. Chem. 2007; 72: 2737
- 4e Correa A, Bolm C. Angew. Chem. Int. Ed. 2007; 46: 8862
- 4f Rao RK, Naidu AB, Jaseer EA, Sekar G. Tetrahedron 2009; 65: 4619
- 4g Verma AK, Singh J, Larock RC. Tetrahedron 2009; 65: 8434
- 4h Zhu L, Li G, Luo L, Guo P, Lan J, You J. J. Org. Chem. 2009; 74: 2200
- 4i Sreedhar B, Shiva Kumar KB, Srinivas P, Balasubrahmanyam V, Venkanna GT. J. Mol. Catal. A: Chem. 2007; 265: 183
- 4j Yang X, Xing H, Zhang Y, Lai Y, Zhang Y, Jiang Y, Ma D. Chin. J. Chem. 2012; 30: 875
- 4k Liu S, Zhou J. New J. Chem. 2013; 37: 2537
- 4l Larsson P.-F, Correa A, Carril M, Norrby P.-O, Bolm C. Angew. Chem. Int. Ed. 2009; 48: 5691
- 4m Swapna K, Murthy SN, Nageswar YV. D. Eur. J. Org. Chem. 2010; 6678
- 5a Barton DH. R, Finet J.-P, Khamsi J. Tetrahedron Lett. 1988; 29: 1115
- 5b Barton DH. R, Finet J.-P, Khamsi J. Tetrahedron Lett. 1986; 27: 3615
- 6 Beach MJ, Hope R, Klaubert DH, Russell RK. Synth. Commun. 1995; 25: 2165
- 7 Mederski WW. K. R, Lefort M, Germann M, Kux D. Tetrahedron 1999; 55: 12757
- 8 Beletskaya IP, Cheprakov AV. Organometallics 2012; 31: 7753
- 9a Ishii H, Sugiura T, Akiyama Y, Ichikawa Y, Watanabe T, Murakami Y. Chem. Pharm. Bull. 1990; 38: 2118
- 9b Ishii H, Takeda H, Hagiwara T, Sakamoto M, Kogusuri K. J. Chem. Soc., Perkin Trans. 1 1989; 2407
- 10a Brown JA. Tetrahedron Lett. 2000; 41: 1623
- 10b Yamazaki K, Nakamura Y, Kondo Y. J. Org. Chem. 2003; 68: 6011
- 10c Vieira TO, Meaney LA, Shi Y.-L, Alper H. Org. Lett. 2008; 10: 4899
- 11a Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400
- 11b Lindley J. Tetrahedron 1984; 40: 1433
- 11c Kunz K, Scholz U, Ganzer D. Synlett 2003; 2428
- 11d Beletskaya IP, Cheprakov AV. Coord. Chem. Rev. 2004; 248: 2337
- 11e Corbet J.-P, Mignani G. Chem. Rev. 2006; 106: 2651
- 11f Ma D, Zhang Y, Yao J, Wu S, Tao F. J. Am. Chem. Soc. 1998; 120: 12459
- 11g Yamada K, Kurokawa T, Tokuyama H, Fukuyama T. J. Am. Chem. Soc. 2003; 125: 6630
- 12 Wang R, Shi H.-F, Zhao J.-F, He Y.-P, Zhang H.-B, Liu J.-P. Bioorg. Med. Chem. Lett. 2013; 23: 1760
- 13 Choi JH, Lim HJ. Org. Biomol. Chem. 2015; 13: 5131
- 14 Kim H.-Y, Yoon J.-Y, Yun J.-H, Cho K.-W, Lee S.-H, Rhee Y.-M, Jung H.-S, Lim HJ, Lee H, Choi J, Heo J.-N, Lee W, No K.-T, Min D, Choi K.-Y. Cell Death Differ. 2015; 22: 912
For reviews of metal-catalyzed N-arylation of indoles, see
For reviews and selected reports, see: