N-Thio- and N-selenophenacylamidines: electrophilic activation as a route to some 1-hetero-3-aza-4-dimethylaminobuta-1,3-dienes

Autor:	Didier Dubreuil, Renée Danion-Bougot, G. T. Manh, Loïc Toupet, Jean Paul Pradere, Franck Purseigle, Daniel Danion, André Guingant
Rok vydání:	1999
Předmět:	chemistry.chemical_classification Tosyl azide chemistry.chemical_compound chemistry Double bond Heteroatom Electrophile Thio Organic chemistry Silver acetate Medicinal chemistry Cycloaddition Reactive site
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :2821-2828
ISSN:	1364-5463 0300-922X
DOI:	10.1039/a903150b
Popis:	The preparation of 2-phenyl-4-dimethylamino-1-aza-, 1-oxa-, 1-thia-, 1-selena-3-azabuta-1,3-dienes as well as their 4-methyl derivatives is described following a new heteroatom interchange reaction process. Heteronucleophilic attack at one particular reactive site of bis-electrophilic amidinium salts is the key feature of the process. In addition, we also disclose that the substituted 1-oxa-3-aza- and 1,3-diazabuta-1,3-dienes can be obtained by a reactional transformation cascade initiated by either silver acetate addition or tosyl azide [3+2] cycloaddition onto the CS or CSe double bonds of the 1-thia- and 1-selena-3-azabuta-1,3-diene analogues.
Databáze:	OpenAIRE
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