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A new alkaline rearrangement of the benzofuran skeleton. One step transformation of 2‐(2‐benzofuranyl)benzonitriles into ( Z )‐phenylmethyleneisoindolinones
Author(s) -
Guillaumel J.,
Boccara N.,
Demerseman P.,
Royer R.,
Bideau J. P.,
Cotrait M.,
Platzer N.
Publication year - 1990
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.5570270325
Subject(s) - chemistry , benzofuran , potassium hydroxide , alkaline hydrolysis , ring (chemistry) , ethylene glycol , hydrolysis , medicinal chemistry , furan , tetralone , organic chemistry
The alkaline hydrolysis of 2‐(2‐benzofuranyl)benzonitriles 2 by potassium hydroxide under reflux in ethanol stops at the corresponding amides 5 . Using other solvents (ethylene glycol or methoxyethanol) at higher temperatures, one can obtain either the amides 5 , the acids 1 or rearrangement products depending on the experimental conditions. The rearrangement products were identified as ( Z )phenylmethylenedihydroisoindolinones 6 resulting from opening of the furan ring. The structures of the compounds 6 were established by 1 H nmr spectroscopy (nOe) and X‐ray crystallography.