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A challenging synthesis of new 1,3,4-thiadiazole derivatives starting from 2-acylamino-3,3-dichloroacrylonitriles

✍ Scribed by Oleksandr V. Golovchenko; Stepan G. Pilyo; Vladimir S. Brovarets; Alexander N. Chernega; Boris S. Drach

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
92 KB
Volume
15
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

Available 2‐acylamino‐3,3‐dichloroacrylonitriles, when treated with hydrazine hydrate, provide 2‐alkyl‐ or 2‐aryl‐5‐hydrazino‐1,3‐oxazole‐4‐carbonitriles that readily add alkyl or aryl isothiocyanates and the adducts formed recyclize on heating. Finally, the synthesis results in 5‐alkyl(aryl)amino‐1,3,4‐thiadiazol‐2‐yl(acylamino)acetonitriles or the products of their further cyclization, 2‐(5‐amino‐1,3‐ oxazol‐2‐yl)‐1,3,4‐thiadiazole derivatives. The structures of the novel substituted 1,3,4‐thiadiazoles are corroborated spectroscopically as well as by X‐ray diffraction method. © 2004 Wiley Periodicals, Inc. Heteroatom Chem 15:454–458, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20041

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