Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Synthesis and Tautomerism of Novel Quinoxalines (Part I)

새로운 Quinoxaline류의 합성과 토토머화 현상 (제1보)

  • Ho Sik Kim (Department of Chemistry, Catholic University of Daegu) ;
  • Jin Hee Kim (Department of Chemistry, Catholic University of Daegu)
  • 김호식 (대구가톨릭대학교 자연대 화학과) ;
  • 김진희 (대구가톨릭대학교 자연대 화학과)
  • Published : 2003.06.20
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Abstract

The reaction of 3-(1-ethoxycarbonyl)ethyl-1,2-dihydro-2-oxoquinoxaline (8) with hydrazine hydrate gave 3-(1-hydrazinocarbonyl)ethyl-2-hydroxyquinoxaline (9). The reaction of compound 9 with substituted benzaldehydes and heteroaryl aldehydes afforded 2-hydroxyquinoxalines (10-12), respectively. The reaction of compound 9 with alkyl (ethoxymethylene)cyanoacetates and ethoxymethylenemalononitrile resulted in the intramolecular cyclization to give the 5-amino-1-[2-(3-hydroxyquinoxalin-2-yl)propanoyl]-pyrazoles (13), respectively. Compounds 10-13 showed the tautomerism between the lactam and lactim forms in dimethyl sulfoxide solution. The tautomer ratios were determined by the $^1H$ NMR. The herbicidal and fungicidal activities of the synthesized compounds were investigated.

3-(1-Ethoxycarbonyl)ethyl-1,2-dihydro-2-oxoquinoxaline(8)을 hydrazine hydrate와 반응시켜 3-(1-hydrazinocarbonyl)ethyl-2-hydroxyquinoxaline(9)을 합성하였고, 화합물 9를 치환 벤즈알데하이드류 또는 heteroaryl aldehyde류와 반응시켜 2-hydroxyquinoxaline류(10-12)를 합성하였다. 또한 화합물 9를 alkyl (ethoxymethylene)- cyanoacetate류 또는 ethoxymethylenemalononitrile과 반응시켜 분자내 고리화반응에 의하여 5-amino-1-[2-(3-hydroxyquinoxalin-2-yl)propanoyl]-pyrazole류(13)를 합성하였다. 얻어진 화합물 10-13은 dimethyl sulfoxide 용액에서 lactam형과 lactime형 사이에 토토머화 현상을 나타내었는데, 이들의 토토머 비를 $^1H$ NMR로서 측정하였다. 그리고 합성한 화합물들에 대한 제초력과 살균력도 조사하였다.

Keywords

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