Solution phase synthesis of arylbenzoxazoles
AssigneeIRM LLC, a Delaware LLC
InventorsJunbiao Chang, Shifeng Pan
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Abstract
This invention provides methods for the solution-phase synthesis of arylbenzoxazoles. The methods involve condensation of aminophenols with benzaldehydes to form a Schiff base. The Schiff base is then induced to undergo oxidative cyclization in the presence of DDQ. The resulting arylbenzoxazoles can be separated from the reduced DDQ byproduct by treatment of reaction mixture with a strongly basic ion exchange resin.
Claims13
A method of synthesizing an arylbenzoxazole or a pharmaceutically acceptable salt thereof, the method comprising:
- (a) condensing an aminophenol and an aromatic aldehyde to form a Schiff base;
- and
- (b) contacting the Schiff base with an oxidizing agent, thereby forming the arylbenzoxazole.
A method of synthesizing a combinatorial library of arylbenzoxazole compounds or pharmaceutically acceptable salts thereof, the method comprising:
- (a) condensing each member of a population of aminophenols with each member of a library of aromatic aldehydes to form a combinatorial library of Schiff bases;
- and
- (b) contacting each member of the combinatorial library of Schiff bases with an oxidizing agent, thereby forming the arylbenzoxazole compounds.
Dependencies are inferred from the claim text.