有机叠氮化合物参与的反应: C—N3基团保留的研究进展

doi:10.6023/cjoc202209022

摘要/Abstract

有机叠氮化合物在天然产物全合成、药物化学以及材料化学等领域有广泛的应用. 叠氮基团在反应过程中倾向于脱除氮气, 转化为多种多样的含氮杂环以及氨基类化合物, 但在许多天然产物全合成的关键步骤中, 都需要保留叠氮基团. 总结了近二十年有机叠氮化合物参与的反应中C—N₃键保留的反应类型, 主要包括环加成反应、与不饱和键的加成、Winstein重排和1,2-叠氮迁移等.

关键词: 有机叠氮化合物, C—N₃键, 环加成, 重排

Organic azides are widely used in the total synthesis of natural products, medicinal chemistry and material chemistry. Azides tend to release molecular nitrogen to construct nitrogen-containing heterocycles or amino compounds. However, the retention of azide is necessary in the critical synthesis steps of some natural products. The types of C—N₃ retention in organic reactions are summarized, including cycloaddition, addition with unsaturated bond, Winstein rearrangement and 1,2-migration.

Key words: organic azide, C—N₃ bond, cycloaddition, rearrangement

引用此文

魏芳, 余鑫, 肖强. 有机叠氮化合物参与的反应: C—N₃基团保留的研究进展[J]. 有机化学, 2023, 43(4): 1365-1385.

Fang Wei, Xin Yu, Qiang Xiao. Advances in C—N₃ Retention Reactions Involving Organic Azides[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1365-1385.

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图/表 44

图式1. 叠氮化合物的转化

Scheme 1. Transformation of azides

图式2. α,β-不饱和酮酸酯与烯基叠氮的hetero-Diels-Alder反应

Scheme 2. Hetero-Diels-Alder reaction of α,β-unsaturated ketone ester and vinyl azides

图式3. α,β-不饱和酮酸酯与二烯基叠氮的Diels-Alder反应

Scheme 3. Diels-Alder reaction of α,β-unsaturated ketone ester and diene azides

图式4. 靛红与共轭二烯基叠氮的环加成反应及芳基酮酸酯与共轭二烯基叠氮的环加成反应

Scheme 4. Cycloaddition of isatin and diene azides and cycloaddition of ketone esters and diene azides

图式5. 分子内的[4＋2]环加成反应

Scheme 5. Intramolecular [4＋2] cycloaddition

图式6. 乙烯基叠氮与N-苯甲酰亚胺的[4＋2]环加成反应

Scheme 6. [4＋2] cycloaddition of N-benzoyl imine and vinyl azide

图式7. 重氮酯与乙烯基叠氮的环丙烷化反应

Scheme 7. Cyclopropanation of diazo esters and azido alkenes

图式8. 重氮酯与烯基叠氮的[3＋2]环加成反应

Scheme 8. [3＋2] Cycloaddition of vinyldiazo and vinylazides

图式9. 环丙烷与烯基叠氮的[3＋2]环加成反应

Scheme 9. [3＋2] Cycloaddition of cyclopropanes and vinylazides

图式10. 环丙烷与烯基叠氮的[3＋2]环加成反应

Scheme 10. [3＋2] Annulation of cyclopropanes and vinylazides

图式11. 叠氮酮的α-H的酸性

Scheme 11. α-H acidity of azido ketones

图式12. 稳定的Ti(IV)烯醇化合物与醛的Aldol反应

Scheme 12. Aldol reaction of stable titanium(IV) enolate and aldehydes

图式13. 叠氮丙酮与醛的Aldol反应

Scheme 13. Aldol reaction of azidoacetone and aldehydes

图式14. 邻位取代的芳香醛的Aldol反应

Scheme 14. Aldol reaction of ortho-substituted aromatic aldehydes

图式15. 邻位无取代基的芳香醛以及α,β-不饱和醛的Aldol反应

Scheme 15. Aldol reaction of ortho-nonsubstituted aromatic aldehydes and α,β-unsaturated aldehydes

图式16. α-叠氮酰胺与三氟甲基炔酮的Aldol反应

Scheme 16. Aldol reaction α-azido amide with alkynyl CF3 ketones

图式17. 与丙酮酸乙酯的Aldol反应

Scheme 17. Aldol reaction with ethyl pyruvate

图式18. 三组分的Mannich反应

Scheme 18. Three component Mannich reaction

图式19. N-硫代膦酰亚胺与α-叠氮酰胺的Mannich反应

Scheme 19. Mannich reactions of N-thiophosphinoyl imines and α-N3 amide

图式20. 亚胺与α-叠氮环己酮的Mannich反应

Scheme 20. Mannich reactions of imine and α-azido cyclic ketones

图式21. 靛红亚胺与α-叠氮酮的Mannich反应

Scheme 21. Mannich reactions of isatin ketimines and α-azido ketone

图式22. 硝基烯烃与α-叠氮酮的Michael加成反应

Scheme 22. Michael addition of nitroolefins and α-azido ketones

图式23. 不饱和酮酸酯与α-叠氮酮的Michael加成反应

Scheme 23. Michael addition of unsaturated ketoesters and α-azido ketones

图式24. Winstein重排

Scheme 24. Winstein rearrangement

图式25. 烯丙基叠氮的环氧化反应

Scheme 25. Epoxidation of allylic azides

图式26. 烯丙基叠氮的动态动力学拆分

Scheme 26. Dynamic kinetic resolution of allylic azides

图式27. Winstein重排与Friedel-Crafts烷基化的串联反应

Scheme 27. Cascade reaction of Winstein rearrangement and Friedel-Crafts alkylation

图式28. 烯丙基叠氮的平衡异构体

Scheme 28. An equilibrium mixture of allylic azide

图式29. Winstein重排与Claisen重排

Scheme 29. Winstein and Claisen rearrangement

图式30. Winstein重排与Overman重排

Scheme 30. Winstein and Overman rearrangement

图式31. 连续Winstein重排过程

Scheme 31. Double Winstein rearrangement

图式32. 硅氢化和硼氢化反应

Scheme 32. Hydrosilylation and hydroboration

图式33. Cope以及Winstein重排过程

Scheme 33. Cope and Winstein rearrangement

图式34. 1,2-叠氮和1,4-氧迁移

Scheme 34. 1,2-Azide and 1,4-oxygen migrations

图式35. 1,2-叠氮迁移

Scheme 35. 1,2-Azide migration

图式36. α,β-不饱和醛与α-叠氮丙酮的串联反应

Scheme 36. Cascade reaction of α,β-unsaturated aldehyde and α-azidoacetone

图式37. 烯基叠氮的分子内氟化环化反应

Scheme 37. Intramolecular fluorocyclization of vinyl azides

图式38. 肉桂基叠氮的Wacker氧化反应

Scheme 38. Wacker oxidation of cinnamyl azides

图式39. 烯基叠氮的卤代烷氧化

Scheme 39. Haloalkoxylation of vinyl azides

图式40. 去对称化反应

Scheme 40. Desymmetrization reaction

图式41. 二叠氮化合物的CuAAC去对称化反应

Scheme 41. Desymmetric CuAAC reaction of diazides

图式42. 二叠氮醇的CuAAC去对称化反应

Scheme 42. Desymmetric CuAAC reaction of diazido alcohols

图式43. 叠氮的外消旋化反应

Scheme 43. Racemization of azides

图式44. 光催化的烯丙基叠氮与溴代物的反应

Scheme 44. Photocatalyst reaction of allyl azides and alkyl bromides

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有机叠氮化合物参与的反应: C—N₃基团保留的研究进展

Advances in C—N₃ Retention Reactions Involving Organic Azides

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