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New Approaches to 6-Oxoisoaporphine and Tetrahydroisoquinoline Derivatives

✍ Scribed by Eduardo Sobarzo-Sánchez; Eugenio Uriarte; Lourdes Santana; Ricardo A. Tapia; Paulo Pérez Lourido

Publisher: John Wiley and Sons
Year: 2010
Tongue: German
Weight: 189 KB
Volume: 93
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200900394

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✦ Synopsis

Abstract

2,3‐Dihydro‐6‐hydroxy‐5‐methoxy‐7__H__‐dibenzo[de,h]quinolin‐7‐one, 6‐hydroxy‐5‐methoxy‐7__H__‐dibenzo[de,h]quinolin‐7‐one, and 2‐(6,7‐dimethoxy‐3,4‐dihydroisoquinolin‐1‐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.

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