Reaction of 2- and 4-vinylpyridines with phenacylpyridinium ylids

Autor:	A. N. Kost, S. M. Vinogradova, P. B. Terent'ev
Rok vydání:	1980
Předmět:	Dimethyl acetylenedicarboxylate chemistry.chemical_compound chemistry Stereochemistry Product (mathematics) Organic Chemistry Medicinal chemistry
Zdroj:	Chemistry of Heterocyclic Compounds. 16:506-511
ISSN:	1573-8353 0009-3122
DOI:	10.1007/bf00561349
Popis:	The reaction of 2- and 4-vinylpyridines with 3-substituted phenacylpyridinium ylids takes place regioselectively with the formation of only 6-substituted 1-pyridyl-3-aroylindolizines. The reaction of the same ylids with dimethyl acetylenedicarboxylate gives a mixture of isomeric 6- and 8-substituted 1,2-dicarbomethoxy-3-aroylindolizines. In the analogous reaction of 2-bromo-1-phenacyl-pyridinium ylid, in addition to the corresponding 5-bromoindolizine, the product of its spontaneous cyclization, viz., 4,5-dicarbomethoxy-6-oxo-(6H)-10c-azaacephenanthrylene, was isolated.
Databáze:	OpenAIRE
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