Inverse Electron Demand Diels-Alder-Type Heterocycle Syntheses with 1,2,3-Triazine 1-Oxides: Expanded Versatility.

ABSTRACT

1,2,3-Triazine 1-oxides are remarkably effective substrates for inverse electron demand Diels-Alder reactions. Formed from vinyldiazoacetates via reaction with tert-butyl nitrite, these stable heterocyclic compounds undergo clean nucleophilic addition with amidines to form pyrimidines, with ß-ketocarbonyl compounds and related nitrile derivatives to form polysubstituted pyridines and with 3/5-aminopyrazoles to form pyrazolo[1,5-a]pyrimidines, in high yield. These practical reactions are rapid at room temperature, are base catalyzed, and offer a diversity of structural modifications.