Synthesis of 1,2,3-Triazine Derivatives by Deoxygenation of 1,2,3-Triazine 1-Oxides

Gildardo Rivera, Luca De Angelis, Ammar Al-Sayyed, Soumen Biswas, 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

G. Rivera, L. De Angelis, A. Al-Sayyed, S. Biswas, H. Arman, M. P. Doyle, Org. Lett., 2022, 24, 6543-6547.

DOI: 10.1021/acs.orglett.2c02484

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Abstract

Trialkyl phosphites mediate a convenient, efficient, and inexpensive deoxygenation of 1,2,3-triazine 1-oxide for the synthesis of 1,2,3-triazine derivatives in high yield. Triethyl phosphite is more reactive than trimethyl phosphite, and both phosphites form their corresponding phosphates in these reactions.

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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.

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Key Words

1,2,3-Triazines, Triethylphosphite, Trimethylphoshite

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ID: J54-Y2022