Benzofuroxan으로부터 Quinoxaline 유도체의 합성(제2보)
Synthesis of Quinoxaline Derivatives from Benzofuroxan(Part II)
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초록
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.
Abstract
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 anhydridesafforded 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.
참고문헌 (3)
- Cheeseman, "R. F. The Chemistry of Heterocyclic Compounds. Condensed Pyrazines", pp.1~290 (1979)
- "Organic Syntheses, Collective", collective, pp.74~78 (1963), John Wiley & Sons
- "P. Advances in Heterocyclic Chemistry Suppl. 1. Tautomerism of Heterocycles" (1976), Academic Press