Reaction of 2- and 4-(Arylmethylideneamino)phenols with Methyl 1-Bromocyclohexanecarboxylate and Zinc

2- and 4-(Arylmethylideneamino)phenols react with Reformatsky reagent, obtained from methyl 1-bromocyclohexanecarboxylate and zinc, to form 3-aryl-2-[2-(or 4-)hydroxyphenyl]-2-azaspiro[3.5]nonan-1-ones. The reaction involves the initial addition of the organozinc reagent across the C=N double bond of the Schiff base and the subsequent intramolecular cyclization of the adduct via the nucleophilic attack of the nitrogen atom on the ester carbonyl carbon atom. The structures of the products were confirmed by X-ray diffraction analysis.