Reaction of o-(oxiranylmethyl)benzonitriles with sodium borohydride or Grignard reagent/CuI: a new sythesis of substituted 3-alkyl-3,4-dihydroisocoumarins.

A new method for the synthesis of substituted 3-alkyl-3,4-dihydroisocoumarins is described. o-(Oxiranylmethyl)benzonitriles, prepared from isovanillin in five steps, when reacted with nucleophiles such as sodium borohydride or phenylmagnesium chloride/CuI, undergo an intramolecular cyclization to yield the target compounds in good yields, in one pot. [ABSTRACT FROM AUTHOR]