The reaction of ethyl 2-oxo-2H-chromene-3-carboxylate with hydrazine hydrate

Molecules. 2013 Feb 6;18(2):2084-95. doi: 10.3390/molecules18022084.

Abstract

Although salicylaldehyde azine (3) was reported in 1985 as the single product of the reaction of ethyl 2-oxo-2H-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-2H-chromene-3-carbohydrazides 6a-f.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Coumarins / chemical synthesis
  • Coumarins / chemistry*
  • Esters / chemistry
  • Hydrazines / chemistry*
  • Hydrazones / chemical synthesis
  • Hydrazones / chemistry

Substances

  • Coumarins
  • Esters
  • Hydrazines
  • Hydrazones
  • ethyl 2-oxo-2H-chromene-3-carboxylate
  • hydrazine