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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 45, Number 5
JKCSEZ 45(5)
October 20, 2001

Title	Synthesis and Tautomerism of Pyrazoles and N-Phenylethanamides with Quinoxaline Ring Quinoxaline 고리를 가진 Pyrazole류 및 N-Phenylethanamide류의 합성과 토토머화 현상
Author	Ho Sik Kim, Kyung Ok Choi, Hyong Choul Lee, Sam Tag Kwag, Yoshihisa Kurasawa 김호식, 최경옥, 이형철, 곽삼탁, Yoshihisa Kurasawa
Keywords
Abstract	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.
Page	454 - 460
Full Text	PDF

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