and Jae Hyuck HurDepartment of Chemistry, Catholic University of Daegu, Gyeongsan 712-702, Korea(Received April 1, 2004)요약. Benzofuroxan과 ethyl acetoacetate를 반응시켜 2-ethoxycarbonyl-3-methylquinoxaline 1,4-dioxide (8)를합성하고, 이것을 hydrazine hydrate 또는 selenium dioxide와 반응시켜 2-hydrazinocarbonyl-3-methylquinoxaline1,4-dioxide (9) 또는 2-ethoxycarbonyl-3-formylquinoxaline 1,4-dioxide (10)를 합성하였다. 화합물 9를 alkanoylchloride류, benzoyl chloride류, heteroacyl chloride류 및 benzenesulfonyl chloride류와 반응시켜 3-methyl-2-(substituted hydrazinocarbonyl)quinoxaline 1,4-dioxide류 (11-14 )를 합성하였다. 화합물 9를 sodium nitrite와 반응시켜 2-azidocarbonyl- 3-methylquinoxaline 1,4-dioxide (15)를 합성한 다음, 이것을 디옥산/알코올류 용매하에서 환류시켜 Curtius 자리옮김반응에 의한 N-(3-methyl-1,4-dioxoquinoxalin-2-yl)-alkyl carbamate류 (16)를 합성하였다. 그리고화합물 15를 치환 아닐린류와 반응시켜 2-(3-substituted phenylureido)-3-methylquinoxaline 1,4-dioxide류 (17)를 합성하였다. 한편 화합물 10을 benzoic hydrazide 또는 치환 아닐린류와 반응시켜 quinoxaline 1,4-dioxide류 (18, 19)를각각 합성하였다. 그리고 합성한 화합물들에 대한 제초력과 살균력도 조사하였다.주제어 : 퀴녹살린 1,4-디옥사이드류, Curtius 자리옮김반응, 제초력, 살균력ABSTRACT. 2-Ethoxycarbonyl-3-methylquinoxaline 1,4-dioxide (8) was synthesized from benzofuroxan and ethylacetoacetate. The reaction of compound 8 with hydrazine hydrate or selenium dioxide gave 2-hydrazinocarbonyl-3-meth-ylquinoxaline 1,4-dioxide (9) or 2-ethoxycarbonyl-3-formylquinoxaline 1,4-dioxide (10), respectively. The reaction ofcompound 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 9with sodium azide gave 2-azidocarbonyl-3-methylquinoxaline 1,4-dioxide ( 15), and then its refluxing in dioxane/alcoholsresulted in the Curtius rearrangement to give N-(3-methyl-1,4-dioxoquinoxalin-2-yl)-alkyl carbamates (16). The reactionof 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, Curtiu s Rearrangement, Herbicidal Activity, Fungicidal Activity