Preparation of Phenacyl Azides and Their Application Advances in Organic Synthesis

doi:10.6023/cjoc202307009

Abstract

Phenacyl azides, a kind of crucial organic azide, serve as a valuable synthetic substrate in organic synthesis. They have extensive applications in constructing diverse nitrogen-containing compounds. Their straightforward synthetic methods, elevated reactivity and multiple reaction sites enable them to undergo reactions at a single site or simultaneously at multiple sites, resulting in a wide range of reaction types. Based on the significant progress made in organic synthesis in recent years, various preparation methods of phenacyl azides and research results classified according to specific reaction types are mainly reviewed. Representative examples and reaction mechanisms are discussed and analyzed.

Key words: phenacyl azide, preparation, types of reaction, application advance

Cite this article

Chunyan She, Anjing Wang, Shan Liu, Wenming Shu, Weichu Yu. Preparation of Phenacyl Azides and Their Application Advances in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 481-507.

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Fig. & Tab. 57

Scheme 1. Preparation methods of phenacyl azides

Scheme 2. Reaction sites and types of phenacyl azides

Scheme 3. Reaction types of phenacyl azides

Scheme 4. Direct transformation of phenacyl azides

Scheme 5. Denitrogenation/reduction reaction of phenacyl azides

Scheme 6. Palladium or tin(II) catalyzed reduction reaction of phenacyl azides

Scheme 7. Piperidinum acetate catalyzed denitrogenation of phenacyl azides

Scheme 8. Enol acetylation of phenacyl azides

Scheme 9. Photolysis of phenacyl azides

Scheme 10. Oxidation of phenacyl azides by HOF?CH3CN

Scheme 11. Phosphine-mediated conversion of azides into diazo compounds

Scheme 12. One-pot coupling reaction of phenacyl azides

Scheme 13. Addition of carbonyl group in phenacyl azides

Scheme 14. Carbonyl group reduction of phenacyl azides catalyzed by NaBH4 or ADH

Scheme 15. Synthesis of amide compounds by metal-free oxidative cleavage of C—C bonds

Scheme 16. Oxidative amidation mechanism of phenacyl azides

Scheme 17. Copper/TEMPO-promoted denitrogenation and oxidation mechanism of phenacyl azides

Scheme 18. Mg(OtBu)2 catalyzed C—H oxidation of phenacyl azides

Scheme 19. Addition of phenacyl azides

Scheme 20. Base-induced addition of phenacyl azides with aldehydes

Scheme 21. Base-induced mechanism of phenacyl azides with keto aldehydes

Scheme 22. Condensation reaction of phenacyl azides with pyruvate

Scheme 23. One-pot three-component reaction of salicylaldehyde, malononitrile and phenacyl azides

Scheme 24. Conjugate addition of phenacyl azides with acrylonitrile compounds

Scheme 25. Michael addition mechanism of phenacyl azides and isatylidene malononitriles

Scheme 26. Conjugate addition of phenacyl azides with alkenyl oxindoles

Scheme 27. Base promoted, microwave accelerated reaction of phenacyl azides with pyridinium salts of phenacyl bromide

Scheme 28. Synthesis of pyrroles by domino sequence of phenacyl azides

Scheme 29. DBU-mediated coupling reaction of phenacyl azides with aldehydes

Scheme 30. Cycloaddition of phenacyl azides with alkyne

Scheme 31. [3＋2] cycloaddition of phenacyl azides with (iodoethynyl)benzene

Scheme 32. 1,3-Dipolar cycloaddition of phenacyl azides with alkynes

Scheme 33. Cycloaddition of phenacyl azides with 4,5-bis(trimethylsilyl)-1H-1,2,3-triazoles

Scheme 34. 1,3-Dipolar cycloaddition of phenacyl azides with alkynes

Scheme 35. 1,3-Dipolar cycloaddition of phenacyl azides with alkynes

Scheme 36. Synthesis of oxazoles from phenacyl azides by aza-Wittig reaction

Scheme 37. Synthesis of oxazoles from phenacyl azides by aza-Wittig reaction

Scheme 38. Synthesis of pyrroles from phenacyl azides by aza-Wittig reaction

Scheme 39. Cathodic reduction process of phenacyl azides

Scheme 40. Self-cyclization of phenacyl azides

Scheme 41. Radical chain reactions of phenacyl azides

Scheme 42. Dimerization of phenacyl azides

Scheme 43. Self-cyclization of phenacyl azides

Scheme 44. Vilsmeier reaction of phenacyl azides

Scheme 45. Synthesis of trisubstituted pyrrole from phenacyl azides

Scheme 46. Thermal rearrangement of phenacyl azides

Scheme 47. Cyclization of phenacyl azides and o-phenylene- diamines

Scheme 48. Iodine-mediated condensation and cyclization of phenacyl azides

Scheme 49. Denitrogenation and cycloaddition of phenacyl azides

Scheme 50. Mechanism of denitrogenation and cyclization reaction between phenacyl azides and diacetylene diesters

Scheme 51. Cu(OAc)2-Et3N mediated oxidative coupling of phenacyl azides

Scheme 52. Mechanism of base-mediated cycloaddition between phenacyl azides and maleimides

Scheme 53. Mechanism of copper-catalyzed cyclization between phenacyl azides and o-aminophenones

Scheme 54. Denitrogenation and arrangement of phenacyl azides

Scheme 55. Denitrogenation and cyclization of phenacyl azides

Scheme 56. Intermolecular Mannich reaction of phenacyl azides

Scheme 57. Mechanism of denitrogenation/[4＋2] cycloaddition of phenacyl azides

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