Staudinger Condensation for the Preparation of Thiohydantoins

Sandrine Gosling; Chahrazade El Amri; Arnaud Tatibouët

doi:10.1055/s-0033-1338592

Synthesis, Table of Contents

Synthesis 2014; 46(08): 1079-1084
DOI: 10.1055/s-0033-1338592

paper

Staudinger Condensation for the Preparation of Thiohydantoins

Sandrine Gosling

^aInstitut de Chimie Organique et Analytique UMR 7311 – CNRS, Université d’Orléans, BP 6759, 45067 Orléans Cedex 2, France Fax: +33(2)38417281

,

Chahrazade El Amri

^bGEMF UR4-UPMC, Université Pierre et Marie Curie Sorbonne Universités, case courrier 256, 7, quai St Bernard, 75252 Paris Cedex 05, France Email: arnaud.tatibouet@univ-orleans.fr

,

Arnaud Tatibouët*

^aInstitut de Chimie Organique et Analytique UMR 7311 – CNRS, Université d’Orléans, BP 6759, 45067 Orléans Cedex 2, France Fax: +33(2)38417281

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Abstract

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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

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References

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

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