Multicomponent synthesis of substituted 3-styryl-1H-quinoxalin-2-ones in an aqueous medium. Issue 44 (31st October 2018)

• Record Type: Journal Article
• Authors: da Costa, Erivaldo P.; Coelho, Sara E.; de Oliveira, André H.; Araújo, Renata M.; Cavalcanti, Livia N.; Domingos, Josiel B.; Menezes, Fabrício G.
• Is Part Of: Tetrahedron letters. Volume 59:Issue 44(2018)
• Page Start: 3961
• Page End: 3964
• Publication Date: 2018-10-31
• Subjects: Multicomponent synthesis -- Green chemistry -- 3-Styryl-1H-quinoxalin-2-ones; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.09.048
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: One-pot synthesis of 3-styryl-1 H -quinoxalin-2-ones in an aqueous medium is described. Reaction medium consists in o -phenylenediamine, sodium pyruvate and aldehydes. Procedure is easily performed and applied to an interesting scope with good yields. A mechanistic proposal involved sequential condensation reactions is presented. Abstract: A multicomponent synthesis of substituted 3-styryl-1 H -quinoxalin-2-ones is described. Sequential reactions of o -phenylenediamine with sodium pyruvate and aldehydes in 20% aqueous acetic acid containing sodium acetate provided the target products in good to high yields. The reaction is proposed to proceed via initial condensation of the diamine and pyruvate partners followed by an aldol condensation-type mechanism.