Mild Cleavage of N–O Bond of 3,6-Dihydro-1,2-oxazines by Condensation of Aldehydes in Aqueous Media

Autor:	Cyrille Kouklovsky, Robert Lett, Gilles Galvani
Rok vydání:	2015
Předmět:	chemistry.chemical_classification Aqueous solution Organic Chemistry Iminium Oxazines Alcohol Cleavage (embryo) Oxaziridine Medicinal chemistry Enamine chemistry.chemical_compound chemistry Hemiaminal Organic chemistry
Zdroj:	Synlett. 26:1340-1344
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-0034-1380533
Popis:	The nonreductive cleavage of a model 3,6-dihydro-1,2-oxazine by condensation of 2,2-dimethoxyacetaldehyde under aqueous conditions is investigated. Depending on the pH of the solution, the reaction leads either to the N-acylated 1,4-amino alcohol or to the corresponding stable hemiaminal. The formation of the former is believed to proceed through iminium to oxaziridine rearrangement and not through enamine formation, as confirmed by the use of nonenolizable aldehydes. This procedure allows a very mild, nonreductive cleavage of N–O bonds.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0c3bef927a671c1a5a194f22ea5c2625 https://doi.org/10.1055/s-0034-1380533 Zobrazit plný text záznamu