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
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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- ...
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