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http://dx.doi.org/10.5012/jkcs.2004.48.4.385

Synthesis of Quinoxaline Derivatives from Benzofuroxan (Part I)  

Kim, Ho-Sik (Department of Chemistry, Catholic University of Daegu)
Hur, Jae-Hyuck (Department of Chemistry, Catholic University of Daegu)
Publication Information
Journal of the Korean Chemical Society / v.48, no.4, 2004 , pp. 385-393 More about this Journal
Abstract
2-Ethoxycarbonyl-3-methylquinoxaline 1,4-dioxide (8) was synthesized from benzofuroxan and ethyl acetoacetate. The reaction of compound 8 with hydrazine hydrate or selenium dioxide gave 2-hydrazinocarbonyl-3-methylquinoxaline 1,4-dioxide (9) or 2-ethoxycarbonyl-3-formylquinoxaline 1,4-dioxide (10), respectively. The reaction of compound 9 with alkanoyl chlorides, benzoyl chlorides, heteroacyl chlorides, and benzenesulfonyl chlorides afforded 3-methyl-2-(substituted hydrazinocarbonyl)quinoxaline 1,4-dioxides (11-14), respectively. The reaction of compound 9 with sodium azide gave 2-azidocarbonyl-3-methylquinoxaline 1,4-dioxide (15), and then its refluxing in dioxane/alcohols resulted in the Curtius rearrangement to give N-(3-methyl-1,4-dioxoquinoxalin-2-yl)-alkyl carbamates (16). The reaction of compound 15 with substituted anilines afforded 2-(3-substituted phenylureido)-3-methylquinoxaline 1,4-dioxides (17). The reaction of compound 10 with benzoic hydrazide or substituted anilines provided quinoxaline 1,4-di-oxides (18, 19), respectively. The herbicidal and fungicidal activities of the synthesized compounds were investigated.
Keywords
Quinoxaline 1,4-Dioxides; Curtius Rearrangement; Herbicidal Activity; Fungicidal Activity;
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