Metal- and solvent-free domino reaction of 2-isocyanophenol esters to benzoxazines: long-range 1,5-acyl migration on 1,4-diazabutatriene
The first example of intramolecular nucleophilic addition of 1,4-diazabutatriene to ester is disclosed. This approach provides a facile and versatile synthesis for functionalized 2H-1,4-benzoxazines under metal-, reagent-, and solvent-free conditions. Experimental and computational studies revealed...
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| Main Authors: | , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
23 April 2024
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| In: |
Chemical communications
Year: 2024, Volume: 60, Issue: 41, Pages: 5451-5454 |
| ISSN: | 1364-548X |
| DOI: | 10.1039/D4CC01214C |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1039/D4CC01214C Verlag, lizenzpflichtig, Volltext: https://pubs.rsc.org/en/content/articlelanding/2024/cc/d4cc01214c 
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| Author Notes: | Alireza Akbari, Hormoz Khosravi, Felix Bauer, Frank Rominger, Bernhard Breit and Saeed Balalaie |
| Summary: | The first example of intramolecular nucleophilic addition of 1,4-diazabutatriene to ester is disclosed. This approach provides a facile and versatile synthesis for functionalized 2H-1,4-benzoxazines under metal-, reagent-, and solvent-free conditions. Experimental and computational studies revealed the pivotal role of 1,5-acyl migration as the self-catalytic step in the reaction selectivity. |
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| Item Description: | Gesehen am 14.03.2025 |
| Physical Description: | Online Resource |
| ISSN: | 1364-548X |
| DOI: | 10.1039/D4CC01214C |