Gold(III) or Gold(I)/Lewis-Acid-Catalyzed Substitution/Cyclization/1,2-Migration Reactions of Propargyl Alcohols with 3-Amino-benzo[ d ]isoxazoles: Synthesis of Pyrimidine Derivatives.

A straightforward synthesis of pyrimidines via Au(III) or Au(I)/Lewis-acid-catalyzed cascade reactions of propargyl alcohols with 3-amino-benzo[ d ]isoxazoles is described. The propargyl amine intermediates are readily generated in situ via oxophilic activation of gold(III) or a Lewis acid, which undergo cyclization/1,2-group migration/aromatization to deliver the desired products. Highly selective 1,2-H or -R 1 migrations are observed in most cases, and the migratory aptitude is dependent on the steric and electronic properties of the propargylic groups.