대한화학회지 (Journal of the Korean Chemical Society)

  • 제29권1호
  • /
  • Pages.61-66
  • /
  • 1985
  • /
  • 1017-2548(pISSN)
  • /
  • 2234-8530(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지

2-아릴-5,6,7,8-테트라히드로-3-신놀린온들의 합성

Synthesis of 2-Aryl-5,6,7,8-tetrahydro-3-cinnolinones

  • 안용현 (서울대학교 자연과학대학 화학과) ;
  • 이윤영 (서울대학교 자연과학대학 화학과)
  • Yong Hyun Ahn (Department of Chemistry, College of Natural Sciences, Seoul National University) ;
  • Youn Young Lee (Department of Chemistry, College of Natural Sciences, Seoul National University)
  • 발행 : 1985.02.20
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초록

2-치환 5,6,7,8-테트라히드로-3-신놀린온 합성에 이용할 2-(2,2,2-트리클로로에틸리덴) 시클로헥산온(1)을 시클로헥산온과 클로랄의 엔아민축합으로 얻고자 하였다. 그러나 1-모르폴리노-1-시클로헥센(2)과 클로랄을 축합한 결과 2-(1-히드록시-2,2,2-트리클로로에틸)시클로헥산온(3)이 생성되었으며, 이것을 탈수시킨 결과 2-(2,2-디클로로비닐)-2-시클로헥센온(4)이 얻어졌다. 화합물 1대신에 ${\alpha}$-(4-모로폴린일)-${\alpha}$-(2-옥소시클로헥실)아세트산 모르폴린일륨(5)을 사용하여 아릴 하드라진들과 반응시킴으로써 2-아릴-5,6,7,8-테트라히드로-3-신놀린올들을 합성할 수 있었다.

The preparation of 2-(2,2,2-trichloroethylidene)cyclohexanone(1), as a key compound for synthesizing 2-substituted 5,6,7,8-tetrahydro-3-cinnolinones, was attempted by the enamine condensation of cyclohexanone with chloral. However, the condensation of 1-morpholino-1-cyclohexene (2) with chloral afforded 2-(1-hydroxy-2,2,2-trichloroethyl) cyclohexanone (3), and its dehydration led to 2-(2,2-dichlorovinyl)-2-cyclohexenone (4). 2-Aryl-5,6,7,8-tetrahydro-3-cinnolinones could be synthesized using morpholinium ${\alpha}$-(4-morpholinyl)-${\alpha}$-(2-oxocyclohexyl)-acetate (5) in place of 1 with arylhydrazines.

키워드

참고문헌

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