A new alkaline rearrangement of the benzofuran skeleton. One step transformation of 2‐(2‐benzofuranyl)benzonitriles into ( Z )‐phenylmethyleneisoindolinones | Zendy

Guillaumel J. | Zendy; Boccara N. | Zendy; Demerseman P. | Zendy; Royer R. | Zendy; Bideau J. P. | Zendy; Cotrait M. | Zendy; Platzer N. | Zendy

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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.

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