Cs₂CO₃-Promoted C(sp²)–N Formation of Dimethyl Thiocarbamate-Protected Indoles Using Tetramethylthiuram Monosulfide (TMTM)

Abstract

An efficient and simple synthesis of 1-thiocarbamoylindoles is reported in which 1H-indoles react with tetramethylthiuram monosulfide (TMTM) to give a series of 1-thiocarbamoylindoles that were obtained­ in good to excellent yields. The procedure was promoted by Cs₂CO₃ under transition-metal-free conditions and gives a simple entry to protected indoles.

Key words

1H-indole - thiuram - transition-metal-free - synthesis - 1-thiocarbamoylindole

• References

• 1 Sundberg RJ. Indoles . Academic Press; London: 1996
• 2 Shiri M. Chem. Rev. 2012; 112: 3508
• 3 Yanagita RC, Nakagawa Y, Yamanaka N, Kashiwagi K, Saito N, Irie K. J. Med. Chem. 2008; 51: 46
• 4 Katritzky AR, Singh SK, Bobrov S. J. Org. Chem. 2004; 69: 9313
• 5 Kingi N, Bergman J. J. Org. Chem. 2016; 81: 7711
• 6 Kutschy P, Suchý M, Dzurilla M, Takasugi M, Kováčik V. Collect. Czech. Chem. Commun. 2000; 65: 1163
• 7 Legocki J, Matysiak J, Niewiadomy A, Kostecka M. J. Agric. Food Chem. 2003; 51: 362
• 8 Doss SH, Mohareb RM, Elmegeed GA, Luoca NA. Pharmazie 2003; 58: 607
• 9 Voss ME, Carter PH, Tebben AJ, Scherle PA, Brown GD, Thompson LA, Xu MZ, Lo YC, Yang GJ, Liu RQ, Strzemienski P, Everlof JG, Trzaskos JM, Decicco CP. Bioorg. Med. Chem. Lett. 2003; 13: 533
• 10 Kang IJ, Wang LW, Hsu SJ, Lee CC, Lee YC, Wu YS, Hsu TA, Yueh A, Chao YS, Chern JH. Bioorg. Med. Chem. Lett. 2009; 19: 4134
• 11 Fukamachi S, Fujita S, Murahashi K, Konishi H, Kobayashi K. Synthesis 2010; 2985
• 12 Kobayashi K, Yamane K, Fukamachi S. Helv. Chim. Acta 2013; 96: 93
• 13 Kaname M, Sashida H. Tetrahedron Lett. 2012; 53: 748
• 14 Sivapriya K, Suguna P, Banerjee A, Saravanan V, Rao DN, Chandrasekaran S. Bioorg. Med. Chem. Lett. 2007; 17: 6387
• 15 Zhang MB, Dally R, Bullock W. Synthetic Commun. 2004; 34: 4023
• 16 Enders D, Rembiak A, Liebich JX. Synthesis 2011; 281
• 17a Zeng MT, Xu W, Liu M, Liu X, Chang CZ, Zhu H, Dong ZB. Synthetic Commun. 2017; 47: 1434
• 17b Zeng MT, Xu W, Liu X, Chang CZ, Zhu H, Dong ZB. Eur. J. Org. Chem. 2017; 6060
• 17c Dong ZB, Liu X, Bolm C. Org. Lett. 2017; 19: 5916
• 18a Zeng MT, Wang M, Peng HY, Cheng Y, Dong ZB. Synthesis 2018; 50: 644
• 18b Cao Q, Peng HY, Cheng Y, Dong ZB. Synthesis 2018; 50: 1527
• 19a Liu X, Liu M, Xu W, Zeng MT, Zhu H, Chang CZ, Dong ZB. Green Chem. 2017; 19: 5591
• 19b Liu X, Zhang SB, Dong ZB. Eur. J. Org. Chem. 2018; 5406
• 19c Peng HY, Dong ZB. Eur. J. Org. Chem. 2019; 949
• 19d Dong ZB, Wang M, Zhu H, Liu X, Chang CZ. Synthesis 2017; 49: 5258