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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 49, Number 4
JKCSEZ 49(4)
August 20, 2005 

 
Title
Synthesis of Quinoxaline Derivatives from Benzofuroxan(Part II)

Benzofuroxan으로부터 Quinoxaline 유도체의 합성(제2보)
Author
Ho Sik Kim*, Jae Hyuck Hur

김호식*, 허재혁
Keywords
퀴녹살린 4-옥사이드류, 분자내 고리화반응, 제초력, 살균력 , Quinoxaline 4-Oxides, Intramolecular Cyclization, Herbicidal Activity, Fungicidal Activity
Abstract
Benzofuroxan과 ethyl acetoacetate를 반응시켜 2-ethoxycarbonyl-3-methylquinoxaline 1,4- dioxide(7)를 합성하고, 이것을 hydrazine hydrate와 반응시켜 2-hydrazinocarbonyl-3-methylquinoxaline 1,4-dioxide(8)를 합성하였다. 화합물 8을 치환 phenylacetyl chloride류, benzyl chloroformate, heteroaryl 알데히드류 및 산무수물들과 반응시켜 3-methyl-2-(substituted hydrazinocarbonyl)quinoxaline 4-oxide류(9-12)를 합성하였다. 또한 화합물 8과 isothiocyanate류를 반응시켜 3-methyl-2-[(N-substituted thiocarbamoyl)hydrazinocarbonyl]quinoxaline 4-oxide류(13)를 합성한 다음, 이것을 2N NaOH 용액에서 환류시켜 분자내 고리화반응에 의한 3-methyl-2-(4-substituted-3-thioxo-1,2,4-triazol-5-yl)quinoxaline 4-oxide류(14)를 합성하였다. 그리고 합성한 화합물들에 대한 제초력과 살균력도 조사하였다.

2-Ethoxycarbonyl-3-methylquinoxaline 1,4-dioxide(7) was synthesized from benzofuroxan and ethyl acetoacetate. The reaction of compound 7 with hydrazine hydrate gave 2-hydrazinocarbonyl-3-methylquinoxaline 1,4-dioxide(8). The reactions of compound 8 with substituted phenylacetyl chlorides, benzyl chloroformate, heteroaryl aldehydes and acid anhydrides afforded 3-methyl-2-(substituted hydrazinocarbonyl)quinoxaline 4-oxides(9-12). The reaction of compound 8 with isothiocyanates afforded 3-methyl-2-[(N-substituted thiocarbamoyl)hydrazinocarbonyl]quinoxaline 4-oxides(13), and followed reflux in 2N NaOH resulted in the intramolecular cyclization to give 3-methyl-2-(4-substituted-3-thioxo-1,2,4-triazol-5-yl)quinoxaline 4-oxides(14). The herbicidal and fungicidal activities of the synthesized compounds were investigated.

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