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Metal- and solvent-free domino reaction of 2-isocyanophenol esters to benzoxazines: long-range 1,5-acyl migration on 1,4-diazabutatriene.
- Source :
-
Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2024 May 16; Vol. 60 (41), pp. 5451-5454. Date of Electronic Publication: 2024 May 16. - Publication Year :
- 2024
-
Abstract
- 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 2 H -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.
Details
- Language :
- English
- ISSN :
- 1364-548X
- Volume :
- 60
- Issue :
- 41
- Database :
- MEDLINE
- Journal :
- Chemical communications (Cambridge, England)
- Publication Type :
- Academic Journal
- Accession number :
- 38689554
- Full Text :
- https://doi.org/10.1039/d4cc01214c