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Molecules 2013, 18(2), 2084-2095; doi:10.3390/molecules18022084

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

1
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
2
Department of Applied Organic Chemistry, National Research Center, Dokki, Cairo 12622, Egypt
3
Department of Medicinal and Pharmaceutical Chemistry, National Research Center, Dokki, Cairo 12622, Egypt
*
Author to whom correspondence should be addressed.
Received: 12 January 2013 / Revised: 29 January 2013 / Accepted: 30 January 2013 / Published: 6 February 2013
(This article belongs to the Section Organic Synthesis)
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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 6af.
Keywords: salicylaldehyde azine; malonohydrazide; coumarins; hydrazides/hydrazones; ring-opening salicylaldehyde azine; malonohydrazide; coumarins; hydrazides/hydrazones; ring-opening
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MDPI and ACS Style

Abdel-Aziz, H.A.; Elsaman, T.; Attia, M.I.; Alanazi, A.M. The Reaction of Ethyl 2-oxo-2H-chromene-3-carboxylate with Hydrazine Hydrate. Molecules 2013, 18, 2084-2095.

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