Premium
Reisert compound studies. VI. The condensation of aldehydes with 2‐benzoyl‐1,2‐dihydroisoquinaldonitrile
Author(s) -
Popp Frank D.,
Gibson Harry W.
Publication year - 1964
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.5570010111
Subject(s) - chemistry , benzoyl chloride , condensation , carbon atom , lithium (medication) , organic chemistry , medicinal chemistry , ring (chemistry) , medicine , physics , thermodynamics , endocrinology
Abstract In 1958 McEwan and coworkers (4) reported the condensation of the lithium salts of 1‐benzoyl‐1,2‐dihydroquinaldonitrile and 2‐benzoyl‐1,2‐dihydroiso‐quinaldonitrile (I) with aldehydes to form esters of secondary alcohols containing the 2‐quinoyl or 1‐iso‐quinoyl (II) group bonded to the carbinol carbon atom. This method was used to devise from appropriate Reissert compounds a convenient synthesis of papaverinol (5) and some attractive intermediates for eventual conversion to the ipecac alkaloids (6).