Canadian journal of chemistry

Condensation of cyclic and acyclic imines with phthalide anions. Synthesis of protoberberines and substituted 3, 4-dihydro-2-methyl-1 (2 H)-isoquinolones

R Marsden, DB MacLean

Index: Marsden, Richard; MacLean, David B. Canadian Journal of Chemistry, 1984 , vol. 62, p. 1392 - 1399

Full Text: HTML

Citation Number: 32

Abstract

3, 4-Dihydroisoquinolines react with anions derived from phthalides and 3-methylphthalides in tetrahydrofuran yielding 13-hydroxy-8-oxotetrahydroprotoberberines and 13-hydroxy-13- methyl-8-oxotetrahydroprotoberberines, respectively. Only one of two possible diastereomers is formed. The lactams may be reduced to the corresponding protoberberines with lithium aluminium hydride. The reaction of the acyclic imine, 3, 4- ...