Advances in C—N3 Retention Reactions Involving Organic Azides

doi:10.6023/cjoc202209022

Abstract

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

Cite this article

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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Fig. & Tab. 44

Scheme 1. Transformation of azides

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

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

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

Scheme 5. Intramolecular [4＋2] cycloaddition

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

Scheme 7. Cyclopropanation of diazo esters and azido alkenes

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

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

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

Scheme 11. α-H acidity of azido ketones

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

Scheme 13. Aldol reaction of azidoacetone and aldehydes

Scheme 14. Aldol reaction of ortho-substituted aromatic aldehydes

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

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

Scheme 17. Aldol reaction with ethyl pyruvate

Scheme 18. Three component Mannich reaction

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

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

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

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

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

Scheme 24. Winstein rearrangement

Scheme 25. Epoxidation of allylic azides

Scheme 26. Dynamic kinetic resolution of allylic azides

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

Scheme 28. An equilibrium mixture of allylic azide

Scheme 29. Winstein and Claisen rearrangement

Scheme 30. Winstein and Overman rearrangement

Scheme 31. Double Winstein rearrangement

Scheme 32. Hydrosilylation and hydroboration

Scheme 33. Cope and Winstein rearrangement

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

Scheme 35. 1,2-Azide migration

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

Scheme 37. Intramolecular fluorocyclization of vinyl azides

Scheme 38. Wacker oxidation of cinnamyl azides

Scheme 39. Haloalkoxylation of vinyl azides

Scheme 40. Desymmetrization reaction

Scheme 41. Desymmetric CuAAC reaction of diazides

Scheme 42. Desymmetric CuAAC reaction of diazido alcohols

Scheme 43. Racemization of azides

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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有机叠氮化合物参与的反应: C—N3基团保留的研究进展