Multicomponent synthesis of substituted 3-styryl-1H-quinoxalin-2-ones in an aqueous medium

[Display omitted] •One-pot synthesis of 3-styryl-1H-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...

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Published inTetrahedron letters Vol. 59; no. 44; pp. 3961 - 3964
Main Authors da Costa, Erivaldo P., Coelho, Sara E., de Oliveira, André H., Araújo, Renata M., Cavalcanti, Livia N., Domingos, Josiel B., Menezes, Fabrício G.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 31.10.2018
Elsevier
Subjects
3-Styryl-1H-quinoxalin-2-ones
Chemistry
Chemistry, Organic
Green chemistry
Multicomponent synthesis
Physical Sciences
Science & Technology
3-Styryl-1H-quinoxalin-2-ones
Multicomponent synthesis
Green chemistry
QUINOXALINE DERIVATIVES
WATER
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Summary:[Display omitted] •One-pot synthesis of 3-styryl-1H-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. A multicomponent synthesis of substituted 3-styryl-1H-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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.09.048