Construction of cyclopentane-fused coumarins via DBU-catalyzed [3+2] cycloaddition of 3-homoacyl coumarins with cyclic 1-azadienes

Huawei Lin; Huimin Yang; Qi Gong; Shan Luo; Jing Gu; Xiaoqun Cao; Biming Mao; Yanqing Ge; Chunhao Yuan

doi:10.1039/D1RA03387E

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Construction of cyclopentane-fused coumarins via DBU-catalyzed [3+2] cycloaddition of 3-homoacyl coumarins with cyclic 1-azadienes†

Huawei Lin,^a Huimin Yang,^a Qi Gong,^a Shan Luo,^a Jing Gu,^a Xiaoqun Cao,^a Biming Mao,*^b Yanqing Ge

*^a and Chunhao Yuan

*^a

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* Corresponding authors

^a School of Chemistry and Pharmaceutical Engineering, Shandong First Medical University, Shandong Academy of Medical Sciences, Taian 271016, Shandong, P. R. China
E-mail: yuanchunhao2017@163.com, geyanqing2016@126.com

^b Institute of Materia Medica, Shandong First Medical University, Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. China
E-mail: maobiming@sdfmu.edu.cn

Abstract

The metal-free DBU catalyzed [3+2] cycloaddition of 3-homoacyl coumarins with cyclic 1-azadienes proceeded smoothly to furnish the corresponding highly functionalized cyclopentane-fused coumarins with excellent diastereoselectivity and complete chemoselectivity and in good yields under mild conditions.

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DOI: https://doi.org/10.1039/D1RA03387E
Article type: Paper
Submitted: 30 Apr 2021
Accepted: 24 May 2021
First published: 04 Jun 2021
This article is Open Access

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RSC Adv., 2021,11, 20118-20122

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Construction of cyclopentane-fused coumarins via DBU-catalyzed [3+2] cycloaddition of 3-homoacyl coumarins with cyclic 1-azadienes

H. Lin, H. Yang, Q. Gong, S. Luo, J. Gu, X. Cao, B. Mao, Y. Ge and C. Yuan, RSC Adv., 2021, 11, 20118 DOI: 10.1039/D1RA03387E

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Construction of cyclopentane-fused coumarins via DBU-catalyzed [3+2] cycloaddition of 3-homoacyl coumarins with cyclic 1-azadienes†

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Construction of cyclopentane-fused coumarins via DBU-catalyzed [3+2] cycloaddition of 3-homoacyl coumarins with cyclic 1-azadienes

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