대한화학회지 (Journal of the Korean Chemical Society)

  • 제45권5호
  • /
  • Pages.454-460
  • /
  • 2001
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  • 1017-2548(pISSN)
  • /
  • 2234-8530(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지

Quinoxaline 고리를 가진 Pyrazole류 및 N-Phenylethanamide류의 합성과 토토머화 현상

Synthesis and Tautomerism of Pyrazoles and N-Phenylethanamides with Quinoxaline Ring

  • 김호식 (대구가톨릭대학교 자연대 화학과) ;
  • 최경옥 (대구가톨릭대학교 자연대 화학과) ;
  • 이형철 (대구가톨릭대학교 자연대 화학과) ;
  • 곽삼탁 (부경대학교 화학공학부) ;
  • Kim, Ho Sik (Department of Chemistry, Catholic University of Taegu) ;
  • Choi, Kyung Ok (Department of Chemistry, Catholic University of Taegu) ;
  • Lee, Hyong Choul (Department of Chemistry, Catholic University of Taegu) ;
  • Kwag, Sam Tag (Division of Chemical Engineering, Pukyong National University) ;
  • Yoshihisa Kurasawa (School of Pharmaceutical Sciences, Kitasato University)
  • 발행 : 20011000
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초록

3-Methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline(7)을 hydrazine hydrate와 반응시켜 3-hydrazinocarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline(8)을 합성하였다. 화합물 8을 alkyl (ethoxymethylene)cyanoacetate류와 반응시켜 [(quinoxalin-2-ylidene)ethanoyl]-1H-pyrazole류(9)를 합성하였고, 화합물 9b를 N-alkylaniline류와 반응시켜 N-alkyl-(quinoxalin-2-ylidene)-N-phenylethanamide류(10)를 합성하였다. 얻어진 화합물 9, 10은 용액에서 enamine 형과 methylene imine 형 사이에 토토머화 현상을 나타내었는데, 이들의 토토머비를 $^1H$ NMR 로서 측정하였다.

The reaction of 3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline(7) with hydrazine hydrate gave 3-hydrazinocarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline(8). The reaction of compound 8 with alkyl (ethoxymethylene)cyanoacetates gave the [(quinoxalin-2-ylidene)ethanoyl]-1H-pyra-zoles(9). The reaction of compound 9b with N-alkylanilines provided the N-alkyl-(quinoxalin-2-ylidene)-N-phenylethanamides(10). Compounds 9 and 10 showed the tautomerism between the enamine and methylene imine forms in solution. The tautomer ratios were determined by the $^1H$ NMR.

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