Reactions of Arylhydrazones of Some α‐Cyanoketones with GRIGNARD Reagents

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Abstract
The arylhydrazones of ethyl α‐oxo‐cyanoacetate 1a–e and the α‐arylhydrazones of β‐phenyl‐α,β‐diketopropionitrile 2a–e, react with GRIGNARD reagents at room temperature to yield the cyanocarbinols 3a–h. On the other hand, 1 and 2 react with phenylmagnesium bromide in refluxing ether‐benzene mixture, to yield the imino derivatives 4a–d. 3a–e are dehydrated by hot acetic acid to yield compounds 5a–d. Similar treatment of 41–d affords the α‐arylazo‐β‐phenylchalcones 6a–d which react with hydroxylamine to yield isoxazoline derivatives 7a–d.Treatment of 1b, d with ethereal diazomethane results in the formation of the N‐methylarylhydrazones 8a, b.The arylhydrazono‐malodinitriles 9 react with GRIGNARD reagents to yield the imino derivatives 10.