Research Progress of 1,3,5-Triazinanes in the Synthesis of Nitrogen-Containing Heterocycles

doi:10.6023/cjoc202107023

Abstract

1,3,5-Triazinanes are an important class of synthons, which could be regarded as the equivalent of formaldehyde imines in constructing various nitrogen-containing heterocyclic skeletons. In recent years, 1,3,5-triazinanes have attracted much attention in the construction of nitrogen-containing heterocyclic compounds. Based on this, the participation of 1,3,5-triazinanes as diatomic, triatomic and four-atom synthons in [2+n], [3+n], [4+n] cycloaddition reactions to construct nitrogen-containing heterocyclic compounds is systematically summarized. Its applications in cycloaddition, heterocyclic chemistry and pharmaceutical chemistry are also summarized. Moreover, the development of 1,3,5-triazinanes in the construction of nitrogen-containing heterocyclic skeletons and their future applications are also prospected.

Key words: 1,3,5-triazinane, nitrogen-containing heterocycle, synthon, cycloaddition reaction, pharmaceutical chemistry

Cite this article

Jiantao Zhang, Peng Zhou, Duoduo Xiao, Weibing Liu. Research Progress of 1,3,5-Triazinanes in the Synthesis of Nitrogen-Containing Heterocycles[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4154-4166.

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Fig. & Tab. 34

Scheme 1. Diverse reaction patterns of 1,3,5-triazinanes

Scheme 2. Au-catalyzed [2+2+2+2] cycloaddition of 1,3,5-triazinanes

Scheme 3. Mg-catalyzed [2+3] or [2⇓+4] cycloaddition of 1,3,5-triazinanes

Scheme 4. Al-catalyzed [2+3] cycloaddition of 1,3,5-triazinanes

Scheme 5. Zn-catalyzed [2+3] cycloaddition of 1,3,5-triazinanes

Scheme 6. Y-catalyzed [2+3] cycloaddition of 1,3,5-triazinanes

Scheme 7. In-catalyzed [2+3] cycloaddition of 1,3,5-triazi- nanes

Scheme 8. Base-promoted [2+3] cycloaddition of 1,3,5-triazinanes with hydroxamate

Scheme 9. Organocatalytic asymmetric [2+3] cycloaddition of 1,3,5-triazinanes

Scheme 10. Cu-catalyzed asymmetric [2⇓+4] cycloaddition of 1,3,5-triazinanes

Scheme 11. Inverse-electron-demand [2⇓+4] cycloaddition of 1,3,5-triazinanes

Scheme 12. Photoredox-catalyzed radical-mediated formation of aza-o-QMs and [2⇓+4] cycloadditions

Scheme 13. [2⇓+4] cycloaddition of para-quinone methides with 1,3,5-triazinanes

Scheme 14. [2⇓+4] cycloaddition of 1,3,5-triazinanes and α,β- unsaturated imines

Scheme 15. Visible light-promoted [2+1] cycloaddition of 1,3, 5-triazinanes and α-diazo esters

Scheme 16. Pd-catalyzed controllable cyclization of vinylethylene carbonates

Scheme 17. Possible mechanism of Pd-catalyzed cyclization of vinylethylene carbonates

Scheme 18. [3+3] step-wise cycloadditions of vinylethylene carbonates

Scheme 19. [3+3] cycloaddition of imines with 1,3,5-triazi- nanes

Scheme 20. [3+3] cycloaddition of α?enolic dithioesters and 1,3,5-triazinanes

Scheme 21. Gold-catalyzed formal [4+1]/[4+3] cycloadditions of 1,3,5-triazinanes with diazo compounds

Scheme 22. Cross-over experiment of gold-catalyzed formal [4+1] cycloadditions

Scheme 23. Tert-butyllithium-promoted [4+1] cycloaddition of triazinanes with phenylhydrazone

Scheme 24. Fe-catalyzed [4+1] cycloadditions of 1,3,5-triazinanes with diazo or diazo analogues

Scheme 25. Cu-catalyzed [4+1] cycloadditions of triazinanes with indole diazo compounds

Scheme 26. Visible light-promoted [4+1] cycloaddition of 1,3, 5-triazinanes and α-diazo esters

Scheme 27. Microwave-promoted synthesis of hexahydropyrimidine-fused 1,4-naphthoquinones from triazinanes

Scheme 28. Gold-catalyzed regiodivergent [4+2] cycloadditions of allenes with triazinanes

Scheme 29. Gold-catalyzed [4+2] cycloadditions of ynamides with triazinanes

Scheme 30. Ring-opening 1-amino-3-aminomethylation of donor-acceptor cyclopropanes

Scheme 31. Gold-catalyzed [4+3] cycloadditions of 2-(1-alky- nyl)-2-alken-1-ones with triazinanes

Scheme 32. [5+2] cycloaddition of azomethine imines with triazinanes

Scheme 33. Rh-catalyzed cyclization of 1,3,5-triazinanes with 1,2,3-triazoles

Scheme 34. Possible mechanism of 1,3,5-triazinanes with 1,2,3-triazoles

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1,3,5-三嗪烷合成含氮杂环的反应研究进展