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2024 , Vol. 44 >Issue 11: 3365 - 3374

DOI: https://doi.org/10.6023/cjoc202404037

研究论文

Brønsted碱促进的β-(2-羟基芳基)乙烯磺酰氟与β,γ-不饱和酮酯(炔酮)串联环化反应合成多取代4H-色烯

  • 唐德林 ,
  • 罗锦昀 ,
  • 杜广芬 ,
  • 蔡志华 ,
  • 何林
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  • 石河子大学化学化工学院 新疆石河子 832000

收稿日期: 2024-05-22

  修回日期: 2024-06-08

  网络出版日期: 2024-07-10

基金资助

国家自然科学基金(21662029); 石河子大学国际合作(GJHZ202204)

收起

Synthesis of Multisubstituted 4H-Chromenes via Brønsted Base- Mediated Tandem Cyclization Reactions of β-(2-Hydroxyaryl) Ethenesulfonyl Fluorides and β,γ-Unsaturated Ketoesters (Ynones)

  • Delin Tang ,
  • Jinyun Luo ,
  • Guangfen Du ,
  • Zhihua Cai ,
  • Lin He
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  • School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832000
*Corresponding authors. E-mail:;

Received date: 2024-05-22

  Revised date: 2024-06-08

  Online published: 2024-07-10

Supported by

National Natural Science Foundation of China(21662029); International Cooperation Project of Shihezi University(GJHZ202204)

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摘要

在20 mol% Cs2CO3催化下, β-(2-羟基芳基)乙烯磺酰氟与炔酮酯在室温下发生分子间/分子内Michael加成反应, 以56%~70%的产率获得11种含磺酰氟基团的多取代4H-色烯衍生物. 此外, 在50 mol% Cs2CO3促进下, β-(2-羟基芳基)乙烯磺酰氟与炔酮在50 ℃下发生类似的串联反应, 以25%~80%的产率得到12种多取代的4H-色烯衍生物.

关键词： β-(2-羟基芳基)乙烯磺酰氟; β,γ-不饱和酮酯(炔酮); 4H-色烯

本文引用格式

唐德林 , 罗锦昀 , 杜广芬 , 蔡志华 , 何林 . Brønsted碱促进的β-(2-羟基芳基)乙烯磺酰氟与β,γ-不饱和酮酯(炔酮)串联环化反应合成多取代4H-色烯[J]. 有机化学, 2024 , 44(11) : 3365 -3374 . DOI: 10.6023/cjoc202404037

Abstract

Under the catalysis of 20 mol% Cs2CO3, β-(2-hydroxyaryl) ethenesulfonyl fluorides reacted with ketoesters throu- gh a tandem intermolecular/intramolecular Michael addition process at room temperature, affording 11 multisubstituted 4H- chromenes bearing a useful sulfonyl fluoride groups in 56%~70% yields. In addition, under the mediation of 50 mol% Cs2CO3, β-(2-hydroxyaryl) ethenesulfonyl fluorides couple with ynones through a similar tandem process at 50 ℃, giving 12 multisubstituted 4H-chromenes in 25%~80% yields.

Key words： β-(2-hydroxyaryl) ethenesulfonyl fluorides; β,γ-unsaturated ketoesters (ynones); 4H-chromenes

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