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Synthesis and Tautomerism of Novel Quinoxalines (Part II)
Synthesis and Tautomerism of Novel Quinoxalines (Part II)
Journal of the Korean Chemical Society. 2003. Aug, 47(4): 345-353
  • Published : August 20, 2003
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Kim, Ho Sik
Choi, Kyung Ok
Lim, Woo Sung

Abstract
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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