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Molecules  2013 

The Reaction of Ethyl 2-oxo-2H-chromene-3-carboxylate with Hydrazine Hydrate

DOI: 10.3390/molecules18022084

Keywords: salicylaldehyde azine, malonohydrazide, coumarins, hydrazides/hydrazones, ring-opening

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Although salicylaldehyde azine ( 3) was reported in 1985 as the single product of the reaction of ethyl 2-oxo-2 H-chromene-3-carboxylate ( 1) with hydrazine hydrate, we identified another main reaction product, besides 3, which was identified as malono-hydrazide ( 4). In the last two decades, however, some articles have claimed that this reaction afforded exclusively hydrazide 2 and they have reported the use of this hydrazide 2 as a precursor in the syntheses of several heterocyclic compounds and hydrazones 6. We reported herein a study of the formation of 2 and a facile route for the synthesis of the target compounds N'-arylidene-2-oxo-2 H-chromene-3-carbohydrazides 6a– f.


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