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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 and Michael P. Doyle*

*Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, United States, Email: michael.doyleutsa.edu

S. Biswas, L. De Angelis, G. Rivera, H. Arman, M. P. Doyle, Org. Lett., 2023, 25, 1104-1108.

DOI: 10.1021/acs.orglett.2c04360



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Abstract

Stable 1,2,3-triazine 1-oxides are remarkably effective substrates for inverse electron demand Diels-Alder reactions. Base-catalyzed reactions with amidines provide pyrimidines, with β-ketocarbonyl compounds and related nitrile derivatives polysubstituted pyridines and with 3/5-aminopyrazoles pyrazolo[1,5-a]pyrimidines in high yield at room temperature.

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Intermolecular [5 + 1]-Cycloaddition between Vinyl Diazo Compounds and tert-Butyl Nitrite to 1,2,3-Triazine 1-Oxides and Their Further Transformation to Isoxazoles

L. De Angelis, H. Zheng, M. T. Perz, H. Arman, M. P. Doyle, Org. Lett., 2021, 23, 6542-6546.


Key Words

Diels-Alder reaction, pyridines


ID: J54-Y2023