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Study of direction of cyclization of 1-azolil-4-aryl/alkyl-thiosemicarbazides

✍ Scribed by Agata Siwek; Monika Wujec; Maria Dobosz; Irena Wawrzycka-Gorczyca

Publisher: John Wiley and Sons
Year: 2010
Tongue: English
Weight: 293 KB
Volume: 21
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.20643

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✦ Synopsis

Abstract

On a four series of 1‐azolil‐4‐aryl/alkyl‐thiosemicabazides, a study on the influence of azole moiety on the capability for intramolecular cyclization and its direction was carried out. It was found that for 4‐aryl/alkyl‐thiosemicabazides with triazole, imidazole, or pyrrole moiety at N‐1 nitrogen atom possible products were only s‐triazoles, both in alkaline and acidic medium. Successful dehydrocyclization of 1‐azolil‐4‐aryl/alkyl‐thiosemicarbazides leading to a thiadiazole has been documented only for a series of 1‐(4‐methyl‐1,2,3‐thiadiazol‐5‐yl‐carbonyl)‐4‐aryl/alkyl‐thiosemicarbazides. It can be speculative that the determination of p__K__~a~ value of oxygen atom of 1‐azolil‐4‐aryl/alkyl‐thiosemicarbazide can be a very valuable parameter in the prediction of the possibility of dehydrocyclization to form thiadiazole. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:521–532, 2010; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20643

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