Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Acetylenic Compounds. XXII. Ring Closure. (4). New Synthesis of Thiazoles and Imidazole.
Yasuo Yura
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1962 Volume 10 Issue 5 Pages 376-382

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Abstract
It was found that the compounds having the general formula RCH(X)-C≡C-R'gave thiazole derivatives by reaction with thiourea. The relationship between the structure of thiazoles and substituent groups was clarified as follows : (1) When R=R'=Ph, 2-amino-4-benzyl-5-phenylthiazole (IId) is obtained, (2) When R=alkyl, R'=H, two kinds of thiazoles are obtained ; and (3) when R=R'=alkyl, thiazole derivative is not obtained. Similarly, propargyl bromide and phenylpropargyl bromide, when reacted with ammonium dithiocarbamate, afforded 2-mercapto-4-methylthiazole (XX) and 2-mercapto-4-benzylthiazole (XXIII), respectively. Further, 2-amino-4-methylimidazole (XXV) was obtained from guanidine and propargyl bromide.
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© The Pharmaceutical Society of Japan
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