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Synthesis of (±)‐laudanoeine and a study of 1‐benzyl‐3‐isoquinoione intermediates
Author(s) -
Elliott I. Wesley
Publication year - 1972
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570090416
Subject(s) - chemistry , tautomer , benzene , derivative (finance) , oxygen , stereochemistry , medicinal chemistry , organic chemistry , financial economics , economics
Abstract A keto acid (2) has been converted to tetrahydropapaverine and (±)‐laudanosine. Some intermediate 3‐isochromanone ( 3 ) and 3‐isoquinolone ( 4 and 5 ) derivatives have been investigated and structures assigned to these compounds from spectroscopic studies. The 3‐isoquinolone tautomer with the o ‐quinonoid structure predominates over the 3‐isoquinolinol form, but the analogous oxygen derivative has preferentially a stilbene structure ( 3 ) with an intact benzene system.