New Approaches to 6-Oxoisoaporphine and Tetrahydroisoquinoline Derivatives
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Date
2010
Journal Title
Journal ISSN
Volume Title
Publisher
WILEY-BLACKWELL
Abstract
2,3-Dihydro-6-hydroxy-5-methoxy-7H-dibenzo[de,h]quinolin-7-one, 6-hydroxy-5-methoxy-7H-dibenzo[de,h]quinolin-7-one, and 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-l-yl)benzyl benzoate, easily available by a Bischler-Napieralski cyclization, were used as starting materials to afford 6-oxoisoaporphine and 2,3-dimethoxy-5,6,8,12b-tetrahydroisoindolo[1,2-a]isoquinoline as the main products. However, the catalytic hydrogenation of the benzyl benzoate derivative afforded, under mild conditions, 1,2,3,4-tetrahydro-6.7-dimethoxy-1 -(2-methylphenyl)isoquinoline.
Description
Keywords
PROTOBERBERINE ALKALOID SYNTHESIS, BORON-TRIFLUORIDE ETHERATE, MENISPERMUM-DAURICUM, OXOISOAPORPHINE ALKALOIDS, AROMATIC DEMETHOXYLATION, REAGENT SYSTEM, ALKYL IODIDES, ALCOHOLS, CONVERSION, CYCLIZATION