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Timmis반응을 이용한 1,3-Dimethyllumazine 유도체의 위치 선택적 합성과 곁사슬반응에 관한 연구

Studies on the Regioselective Synthesis of 1,3-Dimethyllumazine Derivatives by Using the Timmis Reaction and Their Side Chain Reactions

대한화학회지 1999년 43권 5호 p.535 ~ 539
김연희, 김재승, 강용한,
소속 상세정보
김연희 ( Kim Yeon-Hee ) - Hanyang University Department of Chemistry
김재승 ( Kim Jae-Seung ) - Hanyang University Department of Chemistry
강용한 ( Kang Yong-Han ) - Hanyang University Department of Chemistry

Abstract

Timmis반응을 이용하여 1,3-dimthyllumazine유도체를 합성하였다. 4-Amino-1,3-dimethyl-5-nitrosouracil(1)을 2,4-pentanedione, ethyl cyanoacetate, 그리고 ethyl acetoacetat와 반응시켜 6-acetyl-1,3,7-trimethyllumazine (2), ethyl 7-amino-1,3-dimethyllumazine-6-carboxylate (4), ethyl 1,3,7-trimethyl-lumazine-6-carboxylate (5)를 좋은 수율로써 합성하였다. 화합물 2,4,5의 6-아세틸 및 에스테르기에 대한 곁사슬 반응으로 다양한 1,3-dimethyllumazine 유도체들이 합성되었다. 합성된 화합물의 구조 및 물리적 특성은 NMR, UV, IR스펙트럼, 그리고 원소분석에 의하여 확인하였다.

1,3-Dimethyllumazine derivatives were synthesized by using Timmis reaction. The reaction of 4-amino-1,3-dimethyl-5-nitrosouracil(1) with 2,4-pentanedione, ethyl cyanoacetate, and ethyl acetoacetate provided 6-acetyl-1,3,7-trimethyllumazine (2), ethyl 7-amino-1,3-dimethyllumazine-6-carboxylate (4), and ethyl 1,3,7-trimethyllumazine-6-carboxylate (5) in good yieId, respectively. The various 1,3-dimethyllumazine derivatives were prepared from the side chain reactions of 6-acetyl and ester group in compound 2,4, and 5. The structure and physical properties of obtained compounds were characterized NMR, UV, IR spectrum, and elementary analysis.

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