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- Title
1,3-Oxazinan-2-ones via carbonate chemistry: a facile, high yielding synthetic approach.
- Authors
Aricò, Fabio; Bravo, Sara; Crisma, Marco; Tundo, Pietro
- Abstract
A high yielding synthesis of 1,3-oxazinan-2-ones starting from 3-amino-1-propanols and ethylene carbonate (EC) in the presence of catalytic amount of triazabicyclodecene (TBD) is herein reported. The formation of six-membered cyclic carbonates was achieved by intermolecular cyclization reaction via double BAc2 mechanism. Cyclization reactions have been carried out in neat as EC acted both as solvent and reagent. Pure 1,3-oxazinan-2-ones were isolated in high yield by simple liquid-liquid extraction. Further purification can be achieved by recrystallization. The reaction resulted of general application on different substrates including an aryl bis(3-amino-proan-1-ol) compound.
- Subjects
CARBONATES; CHEMICAL yield; CHEMICAL synthesis; ETHYLENE carbonates; PROPANOLS; BICYCLODECENES
- Publication
Pure & Applied Chemistry, 2016, Vol 88, Issue 3, p227
- ISSN
0033-4545
- Publication type
Article
- DOI
10.1515/pac-2015-1004