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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| Main Authors: | , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
June 6, 2022
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| 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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| 520 | |a 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. | ||
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