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Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2 H)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition

Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2 H)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition

Ahmed T A Boraei, Hazem A Ghabbour, Ahmed A M Sarhan, Assem Barakat

ACS Omega. 2020 Mar 3;5(10):5436-5442.

PMID: 32201835

Abstract:

A straightforward green synthesis of 4-methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one 6 is reported from ninhydrin 1 via condensation with ethyl acetoacetate, followed by cyclization with hydrazine hydrate in water as a benign solvent. Tetraazafluoranthen-3-thione 7 was obtained using Lawesson's reagent. N-alkylated tetraazafluoranthen-3-one 8-12 and S-alkylated analogues 13-15 were synthesized via alkylation. The investigation of the unique reactivity of 4-methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one/thione toward the alkylation and aza-Michael additions was explored.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
ALP6358696	Solvent Green 7 hydrate		6358-69-6 (anhydrous)	Price

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