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Synthesis of Quinoxaline Derivatives from Benzofuroxan (Part I)
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 Title & Authors
Synthesis of Quinoxaline Derivatives from Benzofuroxan (Part I)
Kim, Ho-Sik; Hur, Jae-Hyuck;
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 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;
 Language
Korean
 Cited by
1.
Benzofuroxan으로부터 Quinoxaline 유도체의 합성(제2보),김호식;허재혁;

대한화학회지, 2005. vol.49. 4, pp.363-369 crossref(new window)
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