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

Soumen Biswas, Luca De Angelis, Gildardo Rivera, Hadi Arman, Michael P. Doyle

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

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.

Original languageEnglish
Pages (from-to)1104-1108
Number of pages5
JournalOrganic Letters
Volume25
Issue number7
DOIs
StatePublished - 24 Feb 2023

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