Staudinger Condensation for the Preparation of Thiohydantoins

Abstract

An efficient one-pot, two-step sequence starting from azide derivatives is described: first, formation of iminophosphoranes (Staudinger reaction) and condensation with carbon disulfide to form nonisolated isothiocyanates; then, condensation with α-amino esters to provide new N-3-substituted 2-thiohydantoins.

Key words

heterocycles - aza-Wittig reaction - Staudinger condensation - amino acids - thiohydantoins

• References

• 1 Mendgen T, Steuer C, Klein CD. J. Med. Chem. 2012; 55: 743
• 2a Jung ME, Ouk S, Yoo D, Sawyers CL, Chen C, Tran C, Wongvipat J. J. Med. Chem. 2010; 53: 2779
• 2b Yoshino H, Sato H, Shiraishi T, Tachibana K, Emura T, Honma A, Ishikura N, Tsunenari T, Watanabe M, Nishimoto A, Nakamura R, Nakagawa T, Ohta M, Takata N, Furumoto K, Kimura K, Kawata H. Bioorg. Med. Chem. 2010; 18: 8150
• 3 Liu Y, Wu J, Ho P.-Y, Chen L.-C, Chen C.-T, Liang Y.-C, Cheng C.-K, Lee W.-S. Cancer Lett. 2008; 271: 294
• 4 Ermoli A, Bargiotti A, Brasca MG, Ciavolella A, Colombo N, Fachin G, Isacchi A, Menichincheri M, Molinari A, Montagnoli A, Pillan A, Rainoldi S, RiccardiSirtori F, Sola F, Thieffine S, Tibolla M, Valsasina B, Volpi D, Santocanale C, Vanotti E. J. Med. Chem. 2009; 52: 4380
• 5 Ravindranathan KP, Mandiyan V, Ekkati AR, Bae JH, Schlessinger J, Jorgensen WL. J. Med. Chem. 2010; 53: 1662
• 6 Gosling S, Rollin P, Tatibouët A. Synthesis 2011; 3649
• 7 Metwally MA, Abdel-Latif E. J. Sulfur Chem. 2012; 33: 229
• 8 Yong X, Su M, Wan W, You W, Lu X, Qu J, Liu R. New J. Chem. 2013; 37: 1591
• 9a Gasch C, Illangua JM, Merino-Montiel P, Fuentes J. Tetrahedron 2009; 65: 4149
• 9b Aguilar-Moncayo M, Ortiz Mellet C, García Fernández JM, García-Moreno MI. J. Org. Chem. 2009; 74: 3595
• 9c Fuentes J, Salameh BA. B, Angeles Pradera M, Fernández de Córdoba FJ, Gasch C. Tetrahedron 2006; 62: 97
• 9d Tardy S, Lobo Vicente J, Tatibouët A, Dujardin G, Rollin P. Synthesis 2008; 3108
• 10 Fresneda PM, Castaneda M, Sanz MA, Bautista D, Molina P. Tetrahedron 2007; 63: 1849
• 11 Schleiss J. PhD Thesis. University of Orléans; France: 2009
• 12 Pyun M.-S, Choi K.-H, Hong Y.-D, Choi S.-J. Bull. Korean Chem. Soc. 2009; 30: 1187
• 13 Rousseau J, Rousseau C, Lynikaite B, Šačkus A, de Leon C, Rollin P, Tatibouët A. Tetrahedron 2009; 65: 8571