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

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...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 21; no. 5; pp. 991 - 994
Main Authors Zhou, Hui, Mu, Sen, Ren, Bai-Hao, Zhang, Rui, Lu, Xiao-Bing
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2019
Royal Society of Chemistry
Subjects
Alkylidene
Amides
Carbon dioxide
Chemistry
Chemistry, Multidisciplinary
Crystallography
Functional groups
Green & Sustainable Science & Technology
Green chemistry
Oxazolidine
Physical Sciences
Science & Technology
Science & Technology - Other Topics
OLEFINS
CARBON-DIOXIDE
CAPTURE
FIXATION
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Summary: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.
ISSN:1463-9262
1463-9270
DOI:10.1039/c8gc03929a