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

Author:
Zhou, Hui, Mu, Sen, Ren, Bai-Hao, Zhang, Rui, Lu, Xiao-Bing
Source:
Green chemistry 2019 v.21 no.5 pp. 991-994
ISSN:
1463-9270
Subject:
amides, carbon dioxide, green chemistry, moieties, organocatalysts
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.
Agid:
6316348