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Trapping of Thiocarbonyl Ylides with NH-Azoles; A Novel Route to N-Substituted Azoles


Mloston, Grzegorz; Gendek, Tomasz; Heimgartner, Heinz (1998). Trapping of Thiocarbonyl Ylides with NH-Azoles; A Novel Route to N-Substituted Azoles. Polish Journal of Chemistry, 72(1):66-72.

Abstract

The thermal decomposition of 2,5-dihydro-1,3,4-thiadiazoles (1) in the presence of imidazole, pyrazole, 3-phenylpyrazole, and 1,2,4-triazole, respectively, yielded S,N-acetals of type 4. Interception of initially formed thiocarbonyl ylide 2 by the NH-azole is proposed as the reaction mechanism. Treatment of the S,N-acetals 4 with Raney-Ni gave N-substituted azoles 6.

The thermal decomposition of 2,5-dihydro-1,3,4-thiadiazoles (1) in the presence of imidazole, pyrazole, 3-phenylpyrazole, and 1,2,4-triazole, respectively, yielded S,N-acetals of type 4. Interception of initially formed thiocarbonyl ylide 2 by the NH-azole is proposed as the reaction mechanism. Treatment of the S,N-acetals 4 with Raney-Ni gave N-substituted azoles 6.

Citations

8 citations in Web of Science®
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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1998
Deposited On:12 Nov 2013 14:19
Last Modified:05 Apr 2016 17:08
Publisher:Polskie Towarzystwo Chemiczne
ISSN:0137-5083
Funders:Polish State Committee for Scientific Research, Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Official URL:http://www.ichf.edu.pl/pjch/pj-1998/pj0198.htm#66

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