Selective one-pot cascade synthesis of N-substituted highly functionalized pyrroles from unprotected sugars, primary amines, and oxoacetonitriles
A one-pot, three-component cascade reaction between unprotected sugars, primary amines, and 3-oxoacetonitriles gave N-substituted 2,3,5-functionalized pyrroles or N-substituted 2,3,4-functionalized pyrroles in excellent yields and selectivities. The selectivity of the reaction was achieved by simple...
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| Main Authors: | , , |
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| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
2022
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/163328 |
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| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | A one-pot, three-component cascade reaction between unprotected sugars, primary amines, and 3-oxoacetonitriles gave N-substituted 2,3,5-functionalized pyrroles or N-substituted 2,3,4-functionalized pyrroles in excellent yields and selectivities. The selectivity of the reaction was achieved by simple control of the sequence of substrate addition. The reaction showed a wide substrate scope, and various types of sugars, primary amines, and oxoacetonitriles reacted smoothly. The work demonstrates a highly desired simple reaction for embedding nitrogen into sugars to produce valuable N-heterocyclic compounds that are amenable to further modifications to natural products and drug intermediates. |
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