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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 47, Number 3
JKCSEZ 47(3)
June 20, 2003 

 
Title
Synthesis and Tautomerism of Novel Quinoxalines (Part I)

새로운 Quinoxaline류의 합성과 토토머화 현상 (제1보)
Author
Ho Sik Kim, Jin Hee Kim

김호식, 김진희
Keywords
퀴녹살린류, 분자내 고리화반응, 토토머화 현상, 제초력, 살균력 , Quinoxalines, Intramolecular Cyclization, Tautomerism, Herbicidal Activity, Fungicidal Activity
Abstract
3-(1-Ethoxycarbonyl)ethyl-1,2-dihydro-2-oxoquinoxaline(8)을 hydrazine hydrate와 반응시켜 3-(1-hydrazinocarbonyl)ethyl-2-hydroxyquinoxaline(9)을 합성하였고, 화합물 9를 치환 벤즈알데하이드류 또는 heteroaryl aldehyde류와 반응시켜 2-hydroxyquinoxaline류(10-12)를 합성하였다. 또한 화합물 9를 alkyl (ethoxymethylene)- cyanoacetate류 또는 ethoxymethylenemalononitrile과 반응시켜 분자내 고리화반응에 의하여 5-amino-1-[2-(3-hydroxyquinoxalin-2-yl)propanoyl]-pyrazole류(13)를 합성하였다. 얻어진 화합물 10-13은 dimethyl sulfoxide 용액에서 lactam형과 lactime형 사이에 토토머화 현상을 나타내었는데, 이들의 토토머 비를 1H NMR로서 측정하였다. 그리고 합성한 화합물들에 대한 제초력과 살균력도 조사하였다.

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.

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