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Die Synthese von 2-Methyl-5-phenacyl-1,3,4-thiadiazolen / The Synthesis of 2-Methyl-5-phenacyl-1,3,4-thiadiazoles
-
Willi Kantlehner
,
Erwin Haug
Published/Copyright:
June 2, 2014
Keywords
2,5-Dimethyl-1,3,4-thiadiazole (1a) reacts which aromatic carboxylic acid esters 8a - u in the presence of excessive sodium hydride under condensation to give sodium enolates which afford on hydrolysis the phenacyl-1,3,4-thiadiazoles 9a - u. The action of aromatic carboxylic acid chlorides on 1a in the presence of triethylamine gives rise to the formation of mixtures of diacylated thiadiazole derivatives 16 and 18. In some cases the pure 3-acyl-phenacylidene-2,3-dihydro-1,3,4-thiadiazoles 16 can be isolated. Generally the compounds 16 are rearranged on heating in higher boiling solvents to give the enolbenzoates 18. Hydrolysis of the diacylated thiadiazoles 16 and 18 yields the phenacylthiadiazoles 9a, c, d, g - j, v, w.
Received: 2003-11-10
Published Online: 2014-6-2
Published in Print: 2004-4-1
© 1946 – 2014: Verlag der Zeitschrift für Naturforschung
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Keywords for this article
Acylation;
Aromatic Carboxylic Acid Esters and Chlorides;
Phenacyl-1,3,4-thiadiazoles
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