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

1990; Wiley; Volume: 27; Issue: 3 Linguagem: Inglês

10.1002/jhet.5570270325

1943-5193

Jean Guillaumel, Nicole Boccara, P. DEMERSEMAN, René Royer, J. P. Bideau, M. Cotrait, N. Platzer,

Coordination Chemistry and Organometallics

Abstract 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.