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

✍ Scribed by Simon P. J. M. van Nispen; Jacob H. Bregman; Douwe G. van Engen; Albert M. van Leusen; Haruo Saikachi; Tokujiro Kitagawa; Hideaki Sasaki

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
687 KB
Volume
101
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

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.

📜 SIMILAR VOLUMES

Studies on the chemical transformations
Studies on the chemical transformations of rotenoids. 5. Synthesis and cytotoxicity of 1,3-diazepino[5,6-b]benzofuran and pyridazino[4,5-b]benzofurans fused with thiazole, imidazole and pyrimidine
✍ Shin-ichi Nagai; Taisei Ueda; Hiroyuki Sakakibara; Akito Nagatsu; Nobutoshi Mura 📂 Article 📅 1998 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 359 KB

## Abstract Novel benzofuro[2,3‐__d__]pyridazinium chlorides fused with thiazole 5a, imidazole 5b‐c and pyrimidine 5d‐f were prepared starting from 4‐chloropyridazino[4,5‐__b__]benzofuran 3a. Treatment of 5b, 5d and 5e with 10% potassium carbonate solution provided the corresponding free bases 6a‐c