Synthesis and Tautomerism of Novel Quinoxalines (Part II)

새로운 Quinoxaline류의 합성과 토토머화 현상 (제2보)

  • Ho Sik Kim (Department of Chemistry, Catholic University of Daegu) ;
  • Kyung Ok Choi (Department of Chemistry, Catholic University of Daegu) ;
  • Woo Sung Lim (Department of Chemistry, Catholic University of Daegu)
  • 김호식 (대구가톨릭대학교 자연대 화학과) ;
  • 최경옥 (대구가톨릭대학교 자연대 화학과) ;
  • 임우성 (대구가톨릭대학교 자연대 화학과)
  • Published : 2003.08.20


The reaction of 6-chloro-3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline(5) or 3-methoxycarbonylmethylene-6-nitro-2-oxo-1,2,3,4-tetrahydroquinoxaline(6) with hydrazine hydrate gave 3-hydrazinocarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxalines(7, 8). The reaction of compound 7 or 8 with substituted benzaldehydes or heteroaromatic aldehydes afforded quinoxalines(9-14). Compounds showed the tautomerism between the enamine and methylene imine forms, and between the enamine, methylene imine and enaminol forms in dimethyl sulfoxide solution. The tautomer ratios were determined by the 1H NMR.




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