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

doi:10.6023/cjoc202404037

Chinese Journal of Organic Chemistry

ARTICLE

Brønsted碱促进的β-(2-羟基芳基)乙烯磺酰氟与炔酮(酯)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^*

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
基金资助:
国家自然科学基金(No. 21662029)资助项目; 石河子大学国际合作(No. GJHZ202204)资助项目.

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

Tang Delin, Luo Jinyun, Du Guangfen^*, Cai Zhihua, He Lin^*

School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832000

Received:2024-05-22 Revised:2024-06-08
Contact: *E-mail: duguangfen@shzu.edu.cn; helin@shzu.edu.cn
Supported by:
National Natural Science Foundation of China (No. 21662029), the International Cooperation Project of Shihezi University (No. GJHZ201801).

Under the catalysis of 20 mol% Cs₂CO₃, β-(2-hydroxyaryl) ethenesulfonyl fluorides reacted with ketoesters through a tandem intermolecular Michael addition/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

Cite this article

Tang Delin, Luo Jinyun, Du Guangfen, Cai Zhihua, He Lin. Synthesis of Multisubstituted 4H-Chromenes via Brønsted Base-Mediated Tandem Cyclization Reactions of β-(2-hydroxyaryl) Ethenesulfonyl Fluorides and β,γ-Unsaturated Ketoesters (Ynones)[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202404037.

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Brønsted碱促进的β-(2-羟基芳基)乙烯磺酰氟与炔酮(酯)串联环化反应合成多取代4H-色烯

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

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