Synthesis and reactions of 1-cyano-2,2-diphenyl acrylic acid chloride

ABSTRACT

1 Cyano-2-,2-diphenylaciylic acid chloride [I] reacts with aromatic amines yielding the anilides [2a-d], with anthranilic acid the product 2e was converted to the benzoxazone derivative [3]. Reaction of 1 with hydrazine hydrate and benzoyl hydrazine afforded the diaroyl hydrazines [4] and [2g] which are cyclised to the oxadiazole derivatives [5] and [8] respectively. Cyclisation of 4 in acetic anhydride gave pyrazolidine derivative [6].With phenyl hydrazine 1 gave either the anilide [2f] or the pyrazolidine derivative [7]. In the presence of anhydrous aluminium chloride, 1 was converted to the inden-one [9] and/or the ketone [10 a and b]