Metathetic sulfur transfer mediated by N-(2-aminophenyl)-4-methyl-thiazolin-2-thione derivatives: Part III: a new route to diversely substituted S-alkyl thioesters

Mehdid MA, Djafri A, Andreoli F, Vanthuyne N, Farran D, Niebler J, Büttner A, Giorgi M, Roussel C (2013)


Publication Type: Journal article

Publication year: 2013

Journal

Publisher: Elsevier

Book Volume: 69

Pages Range: 4994e5001

DOI: 10.1016/j.tet.2013.04.013

Abstract

A metal free synthesis of S-alkyl thioesters, which does not involve alkylthiol or thiocarboxylic acid as sulfur source is disclosed. The process involves first an acylation at the nitrogen of the readily available N-(2-aminophenyl)-4-methyl-thiazolin-2-thione, second an alkylation at sulfur of the resulting amides and finally a base catalyzed metathetic reaction, which provides under very mild conditions and in high isolated yields the S-alkyl thioesters. An ion-pair intermediate (9-acyl-3-methyl[1,3]thiazolo[3,2-a][3,1]benzimidazol-9-ium alkylthiolate) accounts for the formation of mixed thioesters during cross-coupling experiments.

S-Alkyl diversity is provided by the alkylating agent and the acyl diversity comes from the acylating agent, while the sulfur atom is provided by the heterocycle.

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APA:

Mehdid, M.A., Djafri, A., Andreoli, F., Vanthuyne, N., Farran, D., Niebler, J.,... Roussel, C. (2013). Metathetic sulfur transfer mediated by N-(2-aminophenyl)-4-methyl-thiazolin-2-thione derivatives: Part III: a new route to diversely substituted S-alkyl thioesters. Tetrahedron, 69, 4994e5001. https://dx.doi.org/10.1016/j.tet.2013.04.013

MLA:

Mehdid, Mohammed Amine, et al. "Metathetic sulfur transfer mediated by N-(2-aminophenyl)-4-methyl-thiazolin-2-thione derivatives: Part III: a new route to diversely substituted S-alkyl thioesters." Tetrahedron 69 (2013): 4994e5001.

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