Unexpected result for the acylation of arylhydrazonoethanethioamides

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• 作者：Anastasiya I. Bolgova ; Kseniya I. Lugovik ; Julia O. Subbotina ; Pavel A. Slepukhin ; Vasiliy A. Bakulev ; Nataliya P. Belskaya
• 关键词：Arylhydrazonoethanethioamide ; Acylation ; 1 ; 2 ; 3-Thiadiazole ; Oxidation ; Thiapentalene
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：2 September, 2013
• 年：2013
• 卷：69
• 期：35
• 页码：7423-7429
• 全文大小：769 K

文摘

The acylation of arylhydrazonoethanethioamides containing primary amino group did not yield acylthioamides as expected. Surprisingly, the cyclic 5-acylimino-2,5-dihydro-1,2,3-thiadiazoles were obtained. The formation of thiadiazoles in this reaction was explained by the higher ability of arylhydrazono-N-acylthioacetamide intermediates to be oxidized comparing to their precursors. The presence of pseudobicyclic aromatic structure in the reaction product was a main factor favoring the formation of 1,2,3-thiadiazole ring.