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New Approaches to 6‐Oxoisoaporphine and Tetrahydroisoquinoline Derivatives
Author(s) -
SobarzoSánchez Eduardo,
Uriarte Eugenio,
Santana Lourdes,
Tapia Ricardo A.,
Pérez Lourido Paulo
Publication year - 2010
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200900394
Subject(s) - chemistry , isoquinoline , tetrahydroisoquinoline , derivative (finance) , catalysis , medicinal chemistry , catalytic hydrogenation , organic chemistry , financial economics , economics
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.