108231-23-8Relevant academic research and scientific papers
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.
REACTIONS OF ANALOGS OF THE REISSERT COMPOUNDS SUBSTITUTED WITH POLYNITROBENZYL GROUPS. PART IV., CHLORINATION WITH PHOSPHORUS PENTACHLORIDE
Urbanski, Jerzy,Wrobel, Leszek
, p. 1107 - 1114 (2007/10/02)
All the analogs of Reissert compounds studied here treated with PCl5 undergo solely chlorination, and the reaction usually proceeds similarly to bromination with free bromine.The derivatives of 1,2-dihydroisoquinoline 1 are substituted by a Cl atom (at position 4), while those of 1,2-dihydroquinoline 3 add chlorine to the 3,4-double bond; only the derivatives of 1,4-dihydropyridine 5 add chlorine solely to one of the C=C bonds, as distinguished from the reaction with bromine.The mechanisms of these reactions are discussed as well as the stereochemistry of the products of addition of chlorine to the derivatives of 1,2-dihydroquinoline.
