108133-31-9Relevant 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 III, BROMINATION
Urbanski, Jerzy,Wrobel, Leszek
, p. 1099 - 1106 (2007/10/02)
Of the studied Reissert type compounds analogs treated with bromine 1,2-dihydroisoquinolines (1) undergo substitution (at position 4), 1,2-dihydroquinolines (3) add bromine to the 3,4-diuble bond, whereas the 1,4-dihydropyridine derivatives (5) add bromine to one of the C=C bonds in the first reaction stage (->6a), then they undergo substitution by a bromine atom at position 5 in the next stage (->7).The 3,5-dimethyl derivative 6b merely adds bromine to one of the C=C bonds.The dibromo derivative 6a reacts with 2-propanol to the 2-isopropoxy derivative 8, which further reacts with bromine like 6a.The mechanisms of the reactions studied are discussed.
