Chemistry of Heterocyclic Compounds p. 506 - 511 (1980)
Update date:2022-08-02
Topics: Reaction Experimental
Terent'ev, P. B.
Vinogradova, S. M.
Kost, A. N.
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-phenacylpyridinium 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.
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Doi:10.1039/DT9800001698
(1980)Doi:10.1021/ja01069a017
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(2004)
