Abstract

Whereas, the pentan-2,3,4-trione-3-arylhydrazones (IVa–d) and 1-phenylbutan-1,2,3-trione-2-arylhydrazones (Va–d) undergo the Mannich reaction with formaldehyde and piperdine, 1,3-diphenylpropan-1,2,3-trione-2-arylhydrazones (VIa–d) are recovered unchanged. The ease of cleavage of the acetyl group during the reaction is stressed. A number of the Mannich-bases (VII) react with aromatic thiols to yield the corresponding sulphur analogues (VIII). The arylhydrazones of the triones (IV–VI) undergo 1,2-addition of the Grignard reagent, to the acetyl carbonyl group in IV and V and to the benzoyl carbonyl group in VI, to yield Za–k. Acetophenone is obtained upon chromic acid oxidation of Xa–b; on the otherhand, benzophenone is obtained in the case of Xd. Treatment of Xh and Xj with hydrazine hydrate eliminates the tertiary carbinol moiety with the formation of the hydrazones of the corresponding phenylglyoxal arylhydrazones (XIa–b).

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