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Updated: Aug 10, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Inverse Electron Demand Diels-Alder-Type Heterocycle Syntheses with 1,2,3-Triazine 1-Oxides: Expanded Versatility
Soumen Biswas1, Luca De Angelis1, Gildardo Rivera2
1Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, United States.
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 β-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.
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