Patent ID: 6251689
Filing Date: 2001-06-26
Classification: C07B,C07D,C40B

Abstract:
A process for the solid phase organic synthesis (SPOS) of substituted heterocycles selected from the group consisting of 2-substituted benzimidazoles, 2-substituted benzoxazoles, and 2-substituted benzothiazoles comprising,contacting a resin-bound aldehyde with a 1,2-arylenediamine, 2-aminophenol, 2-aminothiophenol, or substituted derivatives thereof in the presence of an oxidant in a solvent at a temperature and for a time sufficient to form a resin-bound substituted heterocycle selected from the group consisting of 2-substituted benzimidazole, 2-substituted benzoxazole, and 2-substituted benzothiazole andoptionally contacting the formed resin-bound substituted heterocycle selected from the group consisting of 2-substituted benzimidazole, 2-substituted benzoxazole, or 2-substituted heterocycle selected from the group consisting of 2-substituted benzimidazole, 2-substituted benzoxazole, or 2-substituted benzothiazole from the resin, wherein 1) either the aldehyde or the precursor is covalently bound to a resin, forming the solid phase, 2) the oxidant is selected from the group consisting of p-chloranil (CA), 7,7,8,8-tetracyanoquinodimethane (TCNQ), benzylidene-malononitrile (BMCN), tetracyanoethylene (TCNE), 2,3-dicyano-1,4-benzoquinone (DCBQ), or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and 3) the mild conditions include a reaction temperature of room temperature or a temperature of about 40-60.degree. C. and a reaction time of 48 hours or less.