Synthesis of 4-styrylcoumarins via FeCl3-promoted cascade reactions of propargylamines with β-keto esters

Li-Qin Yan; Xiaoting Cai; Xinwei He; Hui Wang; Mengqing Xie; Youpeng Zuo; Yongjia Shang

doi:10.1039/C9OB00323A

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Synthesis of 4-styrylcoumarins via FeCl₃-promoted cascade reactions of propargylamines with β-keto esters†

Li-Qin Yan,^a Xiaoting Cai,^a Xinwei He,

*^a Hui Wang,^a Mengqing Xie,^a Youpeng Zuo^a and Yongjia Shang

*^a

Author affiliations

* Corresponding authors

^a Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P.R. China
E-mail: shyj@mail.ahnu.edu.cn, xinweihe@mail.ahnu.edu.cn

Abstract

A versatile and highly regioselective FeCl₃-promoted tandem cyclization reaction of in situ generated alkynyl o-quinone methides (o-AQMs) with β-keto esters has been developed on the basis of the mode involving an intermolecular 1,4-conjugate addition/alkyne–allene isomerization/intramolecular transesterification/isomerization cascade. Using this method, a variety of diversely substituted 4-styryl-2H-chromen-2-ones were prepared with good efficiency and exclusive site-selectivity.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB00323A
Article type: Paper
Submitted: 09 Feb 2019
Accepted: 20 Mar 2019
First published: 03 Apr 2019

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Org. Biomol. Chem., 2019,17, 4005-4013

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Synthesis of 4-styrylcoumarins via FeCl₃-promoted cascade reactions of propargylamines with β-keto esters

L. Yan, X. Cai, X. He, H. Wang, M. Xie, Y. Zuo and Y. Shang, Org. Biomol. Chem., 2019, 17, 4005 DOI: 10.1039/C9OB00323A

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Organic & Biomolecular Chemistry