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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 40, Number 7
JKCSEZ 40(7)
February 20, 1996 

Synthesis of Naphthacenone Derivatives Using a Michael Reaction

Michael반응을 이용한 Naphthacenone 유도체의 합성
Young S. Rho, Jin H. Yoo, Yoon J. Kwon, Si H. Park, In H. Cho

노영쇠, 유진호, 권윤자, 박시호,조인호
3-Carbomethoxy-1(3H)-isobenzofuranone(9)과 α,β-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.

3-Carbomethoxy-1(3H)-isobenzofuranone(9) underwent condensation with α,β-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.

519 - 525
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