Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Synthesis of Naphthacenone Derivatives Using a Michael Reaction

Michael 반응을 이용한 Naphthacenone 유도체의 합성

  • Rho, Young S. (Department of Chemistry Chonbuk National University) ;
  • Yoo, Jin H. (Department of Chemistry National University) ;
  • Park, Si H. (Department of Chemistry National University) ;
  • Cho, In H. (Department of Chemistry National University) ;
  • Kwon, Yoon J. (Department of Chemistry National University)
  • 노영쇠 (전북대학교 자연과학대학 화학과) ;
  • 유진호 (전북대학교 자연과학대학 화학과) ;
  • 박시호 (전북대학교 자연과학대학 화학과) ;
  • 조인호 (전북대학교 자연과학대학 화학과) ;
  • 권윤자 (전북대학교 자연과학대학 화학과)
  • Published : 19960700
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Abstract

3-Carbomethoxy-1(3H)-isobenzofuranone(9) underwent condensation with ${\alpha}{\beta}-unsaturated$, esters 3a-b to produce the corresponding naphthacene-6,7-diones 11a-b with high yields in one pot procedure. Among the naphthacene-6,7-diones formed, compound 11a without an ethyl group at C-9 position was oxidized to give the naphthacene-5,12-dione 13a, while compound 11b containing the ethyl group was oxidized to give a 3:2 mixture of the naphthacene-5,7,12-trione 12b and naphthacene-5,12-dione 13b under the same experimental conditions.

3-Carbomethoxy-1(3H)-isobenzofuraneme(9)과 .alpha., .beta.-불포화 에스테르 화합물 3a-b를 각각 반응시켜서 naphthacene-6, 7-dione 11a-b를 좋은 수율로 얻었다. 이들 중 C-9 위치에 에틸기가 없는 11a는 산화시켰을 때 naphthacene-5, 12-dione 13a가 생성되는 반면, 에틸기를 갖고 있는 11b는 naphthacene-5, 7, 12-trione 12b와 naphthacene-5, 12-dione 13b가 3:2로 생성되어졌다.

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