1,3,5-三嗪烷合成含氮杂环的反应研究进展

doi:10.6023/cjoc202107023

摘要/Abstract

1,3,5-三嗪烷是一类重要的合成子, 可看成是甲醛亚胺的等价物, 参与各类含氮杂环骨架的构建. 近年来, 1,3,5-三嗪烷在含氮杂环化合物的构建中引起了越来越多的关注. 基于此, 系统综述了1,3,5-三嗪烷作为双原子、三原子以及四原子合成子参与[2+n], [3+n], [4+n]环加成反应构建含氮杂环化合物的反应研究进展, 总结了其在环加成、杂环化学以及药物化学中的应用, 并展望了基于1,3,5-三嗪烷参与构建含氮杂环骨架及其应用的未来发展趋势.

关键词: 1,3,5-三嗪烷, 含氮杂环, 合成子, 环加成反应, 药物化学

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

引用此文

张建涛, 周鹏, 肖朵朵, 刘卫兵. 1,3,5-三嗪烷合成含氮杂环的反应研究进展[J]. 有机化学, 2021, 41(11): 4154-4166.

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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图/表 34

图式1. 1,3,5-三嗪烷的多种反应模式

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

图式2. 金催化1,3,5-三嗪烷[2+2+2+2]环加成

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

图式3. 镁催化1,3,5-三嗪烷[2+3]或[2⇓+4]环加成

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

图式4. 铝催化1,3,5-三嗪烷[2+3]环加成

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

图式5. 锌催化1,3,5-三嗪烷[2+3]环加成

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

图式6. 钇催化1,3,5-三嗪烷[2+3]环加成

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

图式7. 铟催化1,3,5-三嗪烷[2+3]环加成

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

图式8. 碱促进羟肟酸醚与1,3,5-三嗪烷[2+3]环加成

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

图式9. 有机催化1,3,5-三嗪烷[2+3]不对称环加成

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

图式10. 铜催化1,3,5-三嗪烷[2⇓+4]不对称环加成

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

图式11. 1,3,5-三嗪烷逆电子[2⇓+4]环加成

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

图式12. 光氧化还原催化自由基介导的氮杂邻苯醌的生成和[2⇓+4]环加成

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

图式13. 亚甲基对苯醌与1,3,5-三嗪烷[2⇓+4]环加成

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

图式14. α,β-不饱和亚胺与1,3,5-三嗪烷[2⇓+4]环加成

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

图式15. 可见光促进α-重氮酸酯与1,3,5-三嗪烷[2+1]环加成

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

图式16. 钯催化碳酸乙烯酯可控环化反应

Scheme 16. Pd-catalyzed controllable cyclization of vinylethylene carbonates

图式17. 钯催化碳酸乙烯酯环化反应机理

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

图式18. 碳酸乙烯酯分步[3+3]环加成

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

图式19. 亚胺与1,3,5-三嗪烷[3+3]环加成

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

图式20. α-烯醇二硫酯与1,3,5-三嗪烷[3+3]环加成

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

图式21. 金催化1,3,5-三嗪烷与重氮化合物环加成

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

图式22. 金催化[4+1]环加成交叉实验

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

图式23. 叔丁基锂促进三嗪烷与苯腙的[4+1]环加成

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

图式24. 铁催化1,3,5-三嗪烷与重氮/重氮类似物的[4+1]环加成

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

图式25. 铜催化吲哚重氮与三嗪烷的[4+1]环加成

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

图式26. 可见光促进α-重氮酸酯与1,3,5-三嗪烷[4+1]环加成

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

图式27. 微波促进三嗪烷合成六氢嘧啶并1,4-萘醌

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

图式28. 金催化联烯与三嗪烷多样性[4+2]环加成

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

图式29. 金催化炔胺与三嗪烷[4+2]环加成

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

图式30. 推-拉环丙烷开环1-氨基-3-胺甲基化

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

图式31. 金催化炔烯酮与三嗪烷[4+3]环加成

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

图式32. 亚胺叶立德与三嗪烷[5+2]环加成

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

图式33. 铑催化1,2,3-三氮唑与1,3,5-三嗪烷的环化反应

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

图式34. 1,2,3-三氮唑与1,3,5-三嗪烷可能的反应机理

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

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