RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
PDF herunterladen
Synthesis 2015; 47(19): 2991-2996
DOI: 10.1055/s-0034-1380815
DOI: 10.1055/s-0034-1380815
paper
Switchable Copper-Catalyzed Cascade Synthesis of Thiazolidine-2-thiones and Thiazole-2(3H)-thiones
Weitere Informationen
Publikationsverlauf
Received: 06. Februar 2015
Accepted after revision: 17. April 2015
Publikationsdatum:
17. Juni 2015 (online)
Abstract
A novel copper-catalyzed cascade synthesis of thiazolidine-2-thiones from N-(2-bromoallyl)amines and carbon disulfide has been developed. The procedure combines carbamodithioic acid formation and copper-catalyzed intramolecular S-vinylation in one sequence. By elevating the temperature, the one-pot reaction efficiently affords thiazole-2(3H)-thiones in moderate to good yields.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380815.
- Supporting Information
-
References
- 1a Nicolaou KC, Edmonds DJ, Bulger PG. Angew. Chem. Int. Ed. 2006; 45: 7134
- 1b Tietze LF, Brasche G, Gericke KM. Domino Reactions in Organic Synthesis . Wiley–VCH; Weinheim: 2006
- 1c Nicolaou KC, Chen JS. Chem. Soc. Rev. 2009; 38: 2993
- 2 Hündig P. Science (Washington, D.C) 2006; 314: 430
- 3a Rufino AR, Biaggio FC. Tetrahedron Lett. 2001; 42: 8559
- 3b Biaggio FC, Rufino AR, Silveira MC. F. Lett. Org. Chem. 2007; 4: 1
- 4a Farina V, Reeves JT, Senanayake CH, Song JJ. Chem. Rev. 2006; 106: 2734
- 4b Baiget J, Cosp A, Gálvez E, Gómez-Pinal L, Romea P, Urpí F. Tetrahedron 2008; 64: 5637
- 4c Wang J, Liu H.-B, Wang W, Kim I, Ha C.-S. Dalton Trans. 2009; 10422
- 5a Delaunay D, Toupet L, Le Corre M. J. Org. Chem. 1995; 60: 6604
- 5b Gálvez E, Romea P, Urpí F. Org. Synth. 2009; 86: 70
- 5c Morales-Nava R, Fernánandez-Zertuche M, Ordóñez M. Molecules 2011; 16: 8803
- 5d Chen N, Jia WY, Xu JX. Eur. J. Org. Chem. 2009; 5841
- 5e Ziyaei-Halimehjani A, Marjani K, Ashouri A. Tetrahedron Lett. 2012; 53: 3490
- 5f Shi M, Shen YM. J. Org. Chem. 2002; 67: 16
- 6a Zhao QW, Li L, Fang YW, Sun DQ, Li CZ. J. Org. Chem. 2009; 74: 459
- 6b Bryan CS, Braunger JA, Lautens M. Angew. Chem. Int. Ed. 2009; 48: 7064
- 6c You W, Yan XY, Liao Q, Xi CJ. Org. Lett. 2010; 12: 3930
- 7a Mehdid MA, Djafri A, Roussel C, Andreoli F. Molecules 2009; 14: 4634
- 7b Liu H, Jiang XF. Chem. Asian J. 2013; 8: 2546
- 8a Emami S, Hosseinimehr SJ, Shahrbandi K, Enayati AA, Esmaeeli Z. Arch. Pharm. Chem. Life Sci. 2012; 345: 629
- 8b Eid S, Guerro M, Roisnel T, Lorcy D. Org. Lett. 2006; 8: 2377
- 8c Bellec N, Lorcy D, Boubekeur K, Carlier R, Tallec A, Los Sz, Pukacki W, Trybula M, Piekara-Sady L, Robert A. Chem. Mater. 1999; 11: 3147
- 9a Humphlett WJ, Lamon RW. J. Org. Chem. 1964; 29: 2146
- 9b Wolfe DM, Schreiner PR. Eur. J. Org. Chem. 2007; 2825
- 10a Jin HW, Xu XL, Gao JR, Zhong JH, Wang YG. Adv. Synth. Catal. 2010; 352: 347
- 10b Jin HW, Zhou BW, Wu Z, Shen Y, Wang YG. Tetrahedron 2011; 67: 1178
- 10c Zhou BW, Gao JR, Jiang D, Jia JH, Yang ZP, Jin HW. Synthesis 2010; 2794
- 11 Jin HW, Yang YK, Jia JH, Yue BJ, Lang B, Weng JQ. RSC Adv. 2014; 4: 26990
- 12a Dell’Amico DB, Calderazzo F, Labella L, Marchetti F, Pampaloni G. Chem. Rev. 2003; 103: 3857
- 12b Sperotto E, van Klink GP. M, van Koten G, de Vries JG. Dalton Trans. 2010; 39: 10338
- 13 Bowman WR, Bridge CF, Brookes P, Cloonan MO, Leach DC. J. Chem. Soc., Perkin Trans. 1 2002; 58
- 14 Martin DB, Nguyen LQ, Vanderwal CD. J. Org. Chem. 2012; 77: 17
- 15 Liu AH, He LN, Peng SY, Pan ZD, Wang JL, Gao J. Sci. China: Chem. 2010; 53: 1578
- 16 Hanefeld W, Schlitzer M, Von Goesseln J. Arch. Pharm. (Weinheim, Ger.) 1985; 318: 185