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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… Click to show full abstract
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 -R1 migrations are observed in most cases, and the migratory aptitude is dependent on the steric and electronic properties of the propargylic groups.
Journal Title: Organic letters
Year Published: 2022
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