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Synthesis and Tautomerism of Novel Quinoxalines (Part I)

새로운 Quinoxaline류의 합성과 토토머화 현상 (제1보)

  • Published : 2003.06.20

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.

Keywords

Quinoxalines; Intramolecular Cyclization; Tautomerism; Herbicidal Activity; Fungicidal Activity

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