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A regioselective, convergent, and additive-free approach for the synthesis of pyrido[1,4]oxazocines.
- Source :
-
New Journal of Chemistry . 10/21/2023, Vol. 47 Issue 39, p18193-18198. 6p. - Publication Year :
- 2023
-
Abstract
- Research interest in the construction of fused medium-ring [1,4]oxazocines has led to rapid growth in the discovery of biologically active compounds. Herein, the tandem reactions of 4-Cl- and 2-Cl-substituted 3-(oxiran-2-yl)pyridines with a variety of ethanolamines for one-pot synthesis of pyrido[1,4]oxazocines have been developed under additive-free conditions. Note that this process represents a regioselectivity profile in view of the fact that a SN2-type ring-opening reaction of the oxirane moiety with the amino group and a SNAr-type etherification of the 4-chloro or 2-chloropyridine moiety with the hydroxyl group proceed, respectively. Good substrate compatibility, mild reaction conditions, and atom economy make this protocol a convergent and efficient choice for accessing uncommon bicyclic structures. Furthermore, gram-scale reactions and downstream derivatization of the resulting pyrido[1,4]oxazocines are performed. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 11440546
- Volume :
- 47
- Issue :
- 39
- Database :
- Academic Search Index
- Journal :
- New Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 172868132
- Full Text :
- https://doi.org/10.1039/d3nj03776b