Unexpected products from the reaction of different compounds with hydrazine hydrate or aryl thiosemicarbazides

Add time:07/27/2019    Source:sciencedirect.com

The reaction of 2,5-dihydroxyacetophenone I or 1-(1,4-dihydroxynaphthalen-2-yl)ethanone II with various 4-aryl thiosemicarbazides did not yield the expected 4-aryl-1-[1-(2,5-dihydroxyphenyl)ethylidene]thiosemicarbazides III nor 4-aryl-1-[1-(1,4-dihydroxy-naphthalen-2-yl)ethylidene]thiosemicarbazides IV, respectively. However, unexpected products were formed namely, N1,N2-bis[1-(2,5-dihydroxyphenyl)ethylidene]hydrazine V or N1,N2-bis[1-(1,4-dihydroxynaphthalen-2-yl)ethylidene]hydrazine VI, respectively. Also, an unexpected product N1,N2-bis(2,5-dimethoxybenzylidene)hydrazine XI was obtained when heating under reflux diethyl 2-(2,5-dimethoxybenzylidene)propanedioate VII or ethyl 2-cyano-3-(2,5-dimethoxyphenyl)propenoate VIII with 99% hydrazine hydrate in ethanol. The mechanisms of these reactions were proposed.

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