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Heterocyclic Enamides Studies. I. Preparation of 4-Bromo- and 4-Chloroisoquinolines from 1,2-Dihydroisoquinoline Derivatives
Urbanski, Jerzy,Wrobel, Leszek
, p. 417 - 424 (2007/10/02)
The reactions of isoquinoline Reissert compounds analogs 1 with bromine and phosphorus pentachloride as well as the hydrolysis of enamides 1, 2 and 3 have been studied.Compounds 1 treated with bromine in most cases undergo bromination of unsaturated carbon C-4; when treated with PCl5 only 1-phenyl and 1-(2,4,6-trinitrobenzyl) derivatives undergo analogous chlorination.Acidic or basic hydrolysis of starting enamides and their 4-halogeno derivatives results in aromatization with splitting off or retention of substituents at C-1.The sequence of reactions studied can be used as a new interesting route to some 4-bromo or 4-chloroisoquinolines.
