Assembly of functionalized π-extended indolizine polycycles through dearomative [3+2] cycloaddition/oxidative decarbonylation

Shaojing Jin; Lele Wang; Huabin Han; Xiongli Liu; Zhanwei Bu; Qilin Wang

doi:10.1039/D0CC07116A

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Assembly of functionalized π-extended indolizine polycycles through dearomative [3+2] cycloaddition/oxidative decarbonylation†

Shaojing Jin,‡^a Lele Wang,‡^a Huabin Han,^a Xiongli Liu,

^b Zhanwei Bu^a and Qilin Wang

*^a

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* Corresponding authors

^a Institute of Functional Organic Molecular Engineering, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, China
E-mail: wangqilin@henu.edu.cn

^b Guizhou Medicine Edible Plant Resources Research and Development Center, Guizhou University, Guiyang 550025, P. R. China

Abstract

Reported herein is an unexpected construction of functionalized π-extended indolizine polycycles through a one-pot two-step cascade process comprising the base-promoted dearomative [3+2] cycloaddition of quinilinium salts and 3-alkenyl oxindoles, followed by a DDQ-mediated oxidative decarbonylation. Moreover, we could achieve the substrate-controlled diverse synthesis of structurally strained cyclopropane spirooxindole by using pyridinium salts as starting materials.

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DOI: https://doi.org/10.1039/D0CC07116A
Article type: Communication
Submitted: 27 Oct 2020
Accepted: 07 Dec 2020
First published: 08 Dec 2020

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Chem. Commun., 2021,57, 359-362

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Assembly of functionalized π-extended indolizine polycycles through dearomative [3+2] cycloaddition/oxidative decarbonylation

S. Jin, L. Wang, H. Han, X. Liu, Z. Bu and Q. Wang, Chem. Commun., 2021, 57, 359 DOI: 10.1039/D0CC07116A

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Chemical Communications

Assembly of functionalized π-extended indolizine polycycles through dearomative [3+2] cycloaddition/oxidative decarbonylation†

Abstract

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Assembly of functionalized π-extended indolizine polycycles through dearomative [3+2] cycloaddition/oxidative decarbonylation

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