Direct Synthesis of Phosphonates and α-Amino-phosphonates from 1,3-Benzoxazines

Autor:	Oscar Salgado-Escobar, Alexis Hernández-Guadarrama, Ivan Romero-Estudillo, Irma Linzaga-Elizalde
Jazyk:	angličtina
Rok vydání:	2019
Předmět:	phosphonates α-aminophosphonates o-quinone methide o-hydroxybenzylic ethers 1 3-benzoxazines Organic chemistry QD241-441
Zdroj:	Molecules, Vol 24, Iss 2, p 294 (2019)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules24020294
Popis:	A straightforward and novel method for transformation of readily available 1,3-benzoxazines to secondary phosphonates and α-aminophosphonates using boron trifluoride etherate as catalyst is developed. The formation of phosphonates proceeds through ortho-quinone methide (o-QM) generated in situ, followed by a phospha-Michael addition reaction. On the other hand, the α-aminophosphonates were obtained by iminium ion formation and the subsequence nucleophilic substitution of alkylphosphites. This method can be also used for the preparation of o-hydroxybenzyl ethers through oxa-Michael addition.
Databáze:	Directory of Open Access Journals
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