Synthesis of thiazoles and imidazoles from isothiocyanates and tosylmethyl isocyanide. Base-induced ring transformation of 5-amino-1,3-thiazoles to imidazole-5-thiols

Autor:	Hideaki Sasaki, Douwe G. van Engen, Simon P. J. M. van Nispen, Albert M. van Leusen, Jacob H. Bregman, H. Saikachi, Tokujiro Kitagawa
Rok vydání:	2010
Předmět:	Reaction conditions chemistry.chemical_classification chemistry.chemical_compound Transformation (genetics) chemistry Base (chemistry) Stereochemistry Imidazole Tosylmethyl isocyanide General Chemistry Ring (chemistry) Medicinal chemistry
Zdroj:	Recueil des Travaux Chimiques des Pays-Bas. 101:28-34
ISSN:	0165-0513
Popis:	Base-induced cycloadditions of tosylmethyl isocyanide to a series of isothiocyanates have been investigated. Depending on the reaction conditions, thiazoles 5 and/or imidazoles 7 are obtained, with the thiazoles, in particular, being obtained with high regiospecificity. During the course of this work a high-yield ring transformation of 5-amino-1,3-thiazoles (5) to imidazole-5-thiols (7) was discovered, which has not been previously reported. A number of reactions of 7 are described.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f3a4383a6a2e30a344ba5916842444c0 https://doi.org/10.1002/recl.19821010102 Zobrazit plný text záznamu