Synthesis and properties of 3-cyano-4-(4-cyanophenyl)-1,4-dihydropyridine-2(3H)-thiones

Autor:	G. Duburs, A. Krauze
Rok vydání:	2000
Předmět:	chemistry.chemical_compound Chemistry Organic Chemistry Condensation Dihydropyridine medicine Intramolecular cyclization Piperidine Alkylation Medicinal chemistry medicine.drug
Zdroj:	Chemistry of Heterocyclic Compounds. 36:693-697
ISSN:	1573-8353 0009-3122
DOI:	10.1007/bf02297678
Popis:	Piperidinium 3-cyano-4-(4-cyanophenyl)-1,4-dihydropyridine-2(3H)-thiolates were obtained by the condensation of 1,3-dicarbonyl compounds, 4-cyanobenzaldehyde, and cyanothioacetamide in the presence of an equimolar amount of piperidine. The acidification of these thiolates gave the corresponding 1,4-dihydropyridine-2(3H)-thiones and pyridine-2(1H)-thione. Alkylation of 1,4-dihydropyridine-2-thiolates or the reaction mixture of the three-carbon condensation using iodacetamide gave 2-carbamoylmethylthio-1,4,5,6-tetrahydro- or 1,4-dihydropyridines, which were characterized by their conversion to 4,7-dihydrothieno[2,3-b]pyridines.
Databáze:	OpenAIRE
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