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Title: Synthesis of oxazolines and oxazines

Abstract

A process of preparing an oxazoline or oxazine compound of the formula ##STR1## wherein X is an atom selected from the group of oxygen and sulfur, R is selected from the group consisting of C.sub.1-10 alkyl, C.sub.1-10 fluoroalkyl, aryl and substituted-aryl, and n is 2 or 3 comprising ring-closing a compound of the formula ##STR2## wherein X is an atom selected from the group of oxygen and sulfur, R is selected from the group consisting of C.sub.1-10 alkyl, C.sub.1-10 fluoroalkyl, aryl, and substituted aryl, n is 2 or 3, and Y is a bromine or chlorine atom in the presence of a basic reagent consisting essentially of a fluoride salt supported on an inorganic solid substrate is disclosed together with the compounds, 5-bromomethyl-2-phenyl-1,3-oxazoline, 5-methylene-2-phenyl-1,3-oxazine and 4,4-dimethyl-2-vinyl-1,3-oxazoline.

Inventors:
 [1];  [1]
  1. Los Alamos, NM
Issue Date:
Research Org.:
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
OSTI Identifier:
869711
Patent Number(s):
5382665
Assignee:
United States of America as represented by United States (Washington, DC)
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
synthesis; oxazolines; oxazines; process; preparing; oxazoline; oxazine; compound; formula; str1; atom; selected; oxygen; sulfur; consisting; 1-10; alkyl; fluoroalkyl; aryl; substituted-aryl; comprising; ring-closing; str2; substituted; bromine; chlorine; presence; basic; reagent; essentially; fluoride; salt; supported; inorganic; solid; substrate; disclosed; compounds; 5-bromomethyl-2-phenyl-1; 3-oxazoline; 5-methylene-2-phenyl-1; 3-oxazine; 4-dimethyl-2-vinyl-1; atom selected; consisting essentially; fluoride salt; solid substrate; chlorine atom; organic solid; oxazine compound; /999/

Citation Formats

Benicewicz, Brian C, and Mitchell, Michael A. Synthesis of oxazolines and oxazines. United States: N. p., 1995. Web.
Benicewicz, Brian C, & Mitchell, Michael A. Synthesis of oxazolines and oxazines. United States.
Benicewicz, Brian C, and Mitchell, Michael A. Sun . "Synthesis of oxazolines and oxazines". United States. https://www.osti.gov/servlets/purl/869711.
@article{osti_869711,
title = {Synthesis of oxazolines and oxazines},
author = {Benicewicz, Brian C and Mitchell, Michael A},
abstractNote = {A process of preparing an oxazoline or oxazine compound of the formula ##STR1## wherein X is an atom selected from the group of oxygen and sulfur, R is selected from the group consisting of C.sub.1-10 alkyl, C.sub.1-10 fluoroalkyl, aryl and substituted-aryl, and n is 2 or 3 comprising ring-closing a compound of the formula ##STR2## wherein X is an atom selected from the group of oxygen and sulfur, R is selected from the group consisting of C.sub.1-10 alkyl, C.sub.1-10 fluoroalkyl, aryl, and substituted aryl, n is 2 or 3, and Y is a bromine or chlorine atom in the presence of a basic reagent consisting essentially of a fluoride salt supported on an inorganic solid substrate is disclosed together with the compounds, 5-bromomethyl-2-phenyl-1,3-oxazoline, 5-methylene-2-phenyl-1,3-oxazine and 4,4-dimethyl-2-vinyl-1,3-oxazoline.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1995},
month = {1}
}

Works referenced in this record:

Oxazolines. Their preparation, reactions, and applications
journal, October 1971


Alumina-supported fluoride reagents for organic synthesis: optimisation of reagent preparation and elucidation of the active species
journal, January 1986


Calcium fluoride-supported alkali metal fluorides. New reagents for nucleophilic fluorine transfer reactions
journal, January 1986


Fluoride ion Catalysed Michael Reactions
journal, August 1983


Potassium Fluoride on Alumina. An Efficient Solid Base for Elimination, Addition, and Condensation
journal, June 1983


Fluoride Salts on Alumina as Reagents for Alkylation of Phenols and Alcohols
journal, August 1982


The synthesis of 1,4-diketones via fluoride-catalysed Michael addition and supported-permanganate-promoted nef transformation
journal, January 1983


N-ALKYLATION OF AMIDES AND N -HETEROCYCLES WITH POTASSIUM FLUORIDE ON ALUMINA
journal, August 1981