Abstract
A new and effective procedure was developed for the synthesis of 3-ethylquinoxalin-2(1H)-one from o-phenylenediamine and ethyl 2-oxobutanoate. The latter was prepared by the Grignard reaction of diethyl oxalate with ethylmagnesium bromide or iodide. The ethyl group in 3-ethylquinoxalin-2(1H)-one can readily be converted into various functional groups: α-bromoethyl, α-thiocyanato, α-azidoethyl, α-phenylaminoethyl, acetyl, and bromoacetyl. The reaction of 3-(bromoacetyl)quinoxalin-2(1H)-one with thiourea and hydrazine-1,2-dicarbothioamide gives the corresponding 3-(2-amino-4-thiazolyl) derivatives.
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Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 4, 2005, pp. 609–616.
Original Russian Text Copyright © 2005 by Mamedov, Kalinin, Gubaidullin, Isaikina, Litvinov.
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Mamedov, V.A., Kalinin, A.A., Gubaidullin, A.T. et al. Synthesis and Functionalization of 3-Ethylquinoxalin-2(1H)-one. Russ J Org Chem 41, 599–606 (2005). https://doi.org/10.1007/s11178-005-0210-2
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DOI: https://doi.org/10.1007/s11178-005-0210-2