Organocatalyzed carboxylative cyclization of propargylic amides with atmospheric CO2 towards oxazolidine-2,4-diones

Hui Zhou; Sen Mu; Bai-Hao Ren; Rui Zhang; Xiao-Bing Lu

doi:10.1039/C8GC03929A

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Organocatalyzed carboxylative cyclization of propargylic amides with atmospheric CO₂ towards oxazolidine-2,4-diones†

Hui Zhou,

*^a Sen Mu,^a Bai-Hao Ren,^a Rui Zhang^a and Xiao-Bing Lu^a

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* Corresponding authors

^a State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China
E-mail: zhouhui@dlut.edu.cn

Abstract

The metal-free carboxylative cyclization of propargylic amides with CO₂ to oxazolidine-2,4-diones was achieved for the first time employing 1,5,7-triaza-bicyclo-[4.4.0]dec-5-ene (TBD) as an organocatalyst. This method allows for the efficient and selective synthesis of a variety of (Z) 5-alkylidene 1,3-oxazolidine-2,4-diones, and a variety of functional groups are well-tolerated under mild reaction conditions. Theoretical studies reveal that the bifunctional activity (base/H-bond donor) of TBD plays a key role in accelerating this reaction.

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Article information

DOI: https://doi.org/10.1039/C8GC03929A
Article type: Communication
Submitted: 15 Dec 2018
Accepted: 01 Feb 2019
First published: 04 Feb 2019

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Green Chem., 2019,21, 991-994

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Organocatalyzed carboxylative cyclization of propargylic amides with atmospheric CO₂ towards oxazolidine-2,4-diones

H. Zhou, S. Mu, B. Ren, R. Zhang and X. Lu, Green Chem., 2019, 21, 991 DOI: 10.1039/C8GC03929A

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