Direct Synthesis of β-Aminoenals through Reaction of 1,2,3-Triazine with Secondary Amines

Ryan E. Quiñones, Christopher M. Glinkerman, Kaicheng Zhu and Dale L. Boger*

*Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States, Email: bogerscripps.edu

R. E. Quiñones, C. M. Glinkerman, K. Zhu, D. L. Boger, Org. Lett., 2017, 19, 3568-3571.

DOI: 10.1021/acs.orglett.7b01543

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Abstract

Simple and direct nucleophilic addition of secondary amines to 1,2,3-triazine under mild reaction conditions cleanly provides β-aminoenals in good yields. The reaction proceeds by amine nucleophilic addition to C4 of the 1,2,3-triazine, in situ loss of N₂, and subsequent imine hydrolysis.

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proposed mechanism

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Key Words

enaminals

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ID: J54-Y2017