BIOMAT Database Logo BIOMAT Database Logo

Direct Synthesis of Phosphonates and α-Amino-phosphonates from 1,3-Benzoxazines. 2019

Oscar Salgado-Escobar, and Alexis Hernández-Guadarrama, and Ivan Romero-Estudillo, and Irma Linzaga-Elizalde
Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209 Cuernavaca, Morelos, México. pyrel@hotmail.com.

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.

UI MeSH Term Description Entries
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D048588 Benzoxazines OXAZINES with a fused BENZENE ring. Benzoxazine,Benzoxazinoid,Benzoxazinone,Benzoxazinones,Benzoxazinoids
D063065 Organophosphonates Carbon-containing phosphonic acid compounds. Included under this heading are compounds that have carbon bound to either OXYGEN atom or the PHOSPHOROUS atom of the (P Phosphonate,Phosphonates,Phosphonic Acid Esters,Acid Esters, Phosphonic,Esters, Phosphonic Acid

Related Publications

Oscar Salgado-Escobar, and Alexis Hernández-Guadarrama, and Ivan Romero-Estudillo, and Irma Linzaga-Elizalde
Reagent-Controlled Divergent Synthesis of 2-Amino-1,3-Benzoxazines and 2-Amino-1,3-Benzothiazines.
January 2020, The Journal of organic chemistry,
Oscar Salgado-Escobar, and Alexis Hernández-Guadarrama, and Ivan Romero-Estudillo, and Irma Linzaga-Elizalde
Enantioselective Synthesis of α-Amino Phosphonates via Pd-Catalyzed Asymmetric Hydrogenation.
February 2016, Organic letters,
Oscar Salgado-Escobar, and Alexis Hernández-Guadarrama, and Ivan Romero-Estudillo, and Irma Linzaga-Elizalde
Asymmetric synthesis of β-hydroxy-α-amino phosphonic acid derivatives via organocatalytic direct aldol reaction of α-isothiocyanato phosphonates with aldehydes.
October 2013, The Journal of organic chemistry,
Oscar Salgado-Escobar, and Alexis Hernández-Guadarrama, and Ivan Romero-Estudillo, and Irma Linzaga-Elizalde
Copper-catalyzed synthesis of α-hydroxy phosphonates from H-phosphonates and alcohols or ethers.
April 2013, Chemistry, an Asian journal,
Oscar Salgado-Escobar, and Alexis Hernández-Guadarrama, and Ivan Romero-Estudillo, and Irma Linzaga-Elizalde
Direct transformation of amides into α-amino phosphonates via a reductive phosphination process.
August 2013, Organic letters,
Oscar Salgado-Escobar, and Alexis Hernández-Guadarrama, and Ivan Romero-Estudillo, and Irma Linzaga-Elizalde
Synthesis and fungicidal activity of novel 2,3-disubstituted-1,3-benzoxazines.
July 2012, Molecules (Basel, Switzerland),
Oscar Salgado-Escobar, and Alexis Hernández-Guadarrama, and Ivan Romero-Estudillo, and Irma Linzaga-Elizalde
Silver-Catalyzed One-Pot Three-Component Synthesis of α-Aminonitriles and Biologically Relevant α-Amino-phosphonates.
October 2022, Chemistry, an Asian journal,
Oscar Salgado-Escobar, and Alexis Hernández-Guadarrama, and Ivan Romero-Estudillo, and Irma Linzaga-Elizalde
Enantioselective synthesis of α-aryl α-hydrazino phosphonates.
May 2024, Chemical science,
Oscar Salgado-Escobar, and Alexis Hernández-Guadarrama, and Ivan Romero-Estudillo, and Irma Linzaga-Elizalde
The asymmetric synthesis of chiral cyclic α-hydroxy phosphonates and quaternary cyclic α-hydroxy phosphonates.
February 2012, Organic & biomolecular chemistry,
Oscar Salgado-Escobar, and Alexis Hernández-Guadarrama, and Ivan Romero-Estudillo, and Irma Linzaga-Elizalde
Asymmetric Synthesis and Bioselective Activities of α-Amino-phosphonates Based on the Dufulin Motif.
June 2016, Journal of agricultural and food chemistry,
Copied contents to your clipboard!