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The Reaction of Ethyl 2-oxo-2H-chromene-3-carboxylate with Hydrazine Hydrate
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
Department of Applied Organic Chemistry, National Research Center, Dokki, Cairo 12622, Egypt
Department of Medicinal and Pharmaceutical Chemistry, National Research Center, Dokki, Cairo 12622, Egypt
* Author to whom correspondence should be addressed.
Received: 12 January 2013; in revised form: 29 January 2013 / Accepted: 30 January 2013 / Published: 6 February 2013
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.
Keywords: salicylaldehyde azine; malonohydrazide; coumarins; hydrazides/hydrazones; ring-opening
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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.
Abdel-Aziz HA, Elsaman T, Attia MI, Alanazi AM. The Reaction of Ethyl 2-oxo-2H-chromene-3-carboxylate with Hydrazine Hydrate. Molecules. 2013; 18(2):2084-2095.
Abdel-Aziz, Hatem A.; Elsaman, Tilal; Attia, Mohamed I.; Alanazi, Amer M. 2013. "The Reaction of Ethyl 2-oxo-2H-chromene-3-carboxylate with Hydrazine Hydrate." Molecules 18, no. 2: 2084-2095.