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Synthesis of pyrrolidin-5-one-2-carboxamides through cyclization of N-substituted-2-alleneamides

The synthesis of pyrrolidin-5-one-2-carboxamides 6a-p has been developed via a one-pot Ugi reaction of allenic acids, primary amines, isocyanides, and aldehydes followed by regioselective cyclization of the resultant N-substituted-2-allenamides with KOt-Bu at room temperature. The cyclization reacti...

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Bibliographic Details
Main Authors: Shahriari, Azadeh (Author) , Amiri, Kamran (Author) , Nikbakht, Ali (Author) , Rominger, Frank (Author) , Bijanzadeh, Hamid Reza (Author) , Balalaie, Saeed (Author)
Format: Article (Journal)
Language:English
Published: June 6, 2022
In: The journal of organic chemistry
Year: 2022, Volume: 87, Issue: 12, Pages: 7778-7785
ISSN:1520-6904
DOI:10.1021/acs.joc.2c00387
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.joc.2c00387
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Author Notes:Azadeh Shahriari, Kamran Amiri, Ali Nikbakht, Frank Rominger, Hamid Reza Bijanzadeh, and Saeed Balalaie
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Summary:The synthesis of pyrrolidin-5-one-2-carboxamides 6a-p has been developed via a one-pot Ugi reaction of allenic acids, primary amines, isocyanides, and aldehydes followed by regioselective cyclization of the resultant N-substituted-2-allenamides with KOt-Bu at room temperature. The cyclization reaction was carried out through a 5-exo-dig approach, which resulted in good yields and high atom-economy under transition-metal-free and mild reaction conditions.
Item Description:Gesehen am 29.07.2022
Physical Description:Online Resource
ISSN:1520-6904
DOI:10.1021/acs.joc.2c00387

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