芳乙酰叠氮的制备及其在有机合成中的应用进展

doi:10.6023/cjoc202307009

摘要/Abstract

作为一种非常重要的有机叠氮化合物, 芳乙酰叠氮是有机合成中优良的合成子, 可广泛用于构建各种含氮化合物. 它的合成方法简单, 反应活性高, 反应位点多, 不仅可以在一个位点上发生反应, 还可以同时在两个或多个位点上发生反应, 从而使其反应类型相当丰富. 基于近年来芳乙酰叠氮在有机合成中取得了诸多进展, 主要综述了芳乙酰叠氮的各种制备方法以及按照具体的反应类型分类的研究结果, 并对代表性的例子及其反应机理进行了讨论和分析.

关键词: 芳乙酰叠氮, 制备, 反应类型, 应用进展

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

引用此文

佘春艳, 王安静, 刘珊, 舒文明, 余维初. 芳乙酰叠氮的制备及其在有机合成中的应用进展[J]. 有机化学, 2024, 44(2): 481-507.

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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图/表 57

图式1. 芳乙酰叠氮的制备方法

Scheme 1. Preparation methods of phenacyl azides

图式2. 芳乙酰叠氮的反应位点和反应类型

Scheme 2. Reaction sites and types of phenacyl azides

图式3. 芳乙酰叠氮的反应类型

Scheme 3. Reaction types of phenacyl azides

图式4. 芳乙酰叠氮的直接转化

Scheme 4. Direct transformation of phenacyl azides

图式5. 芳乙酰叠氮的脱氮还原反应

Scheme 5. Denitrogenation/reduction reaction of phenacyl azides

图式6. 钯或锡(II)催化芳乙酰叠氮的还原反应

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

图式7. 醋酸哌啶盐催化芳乙酰叠氮的脱氮反应

Scheme 7. Piperidinum acetate catalyzed denitrogenation of phenacyl azides

图式8. 芳乙酰叠氮的烯醇乙酰化反应

Scheme 8. Enol acetylation of phenacyl azides

图式9. 苯乙酰叠氮的光解反应

Scheme 9. Photolysis of phenacyl azides

图式10. HOF?CH3CN氧化苯乙酰叠氮化合物

Scheme 10. Oxidation of phenacyl azides by HOF?CH3CN

图式11. 膦介导的叠氮化合物转化为重氮化合物

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

图式12. 苯乙酰叠氮的一锅偶联反应

Scheme 12. One-pot coupling reaction of phenacyl azides

图式13. 苯乙酰叠氮羰基的加成反应

Scheme 13. Addition of carbonyl group in phenacyl azides

图式14. NaBH4或ADH催化芳乙酰叠氮的羰基还原反应

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

图式15. 无金属氧化裂解C—C键合成酰胺化合物

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

图式16. 苯乙酰叠氮的氧化酰胺化反应机理

Scheme 16. Oxidative amidation mechanism of phenacyl azides

图式17. Cu/TEMPO促进苯乙酰叠氮的脱氮氧化反应机理

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

图式18. Mg(OtBu)2催化苯乙酰叠氮的C—H氧化反应

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

图式19. 芳乙酰叠氮的加成反应

Scheme 19. Addition of phenacyl azides

图式20. 碱诱导苯乙酰叠氮与醛的加成

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

图式21. 碱诱导芳乙酰叠氮与酮醛的反应机理

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

图式22. 芳乙酰叠氮与丙酮酸酯的缩合反应

Scheme 22. Condensation reaction of phenacyl azides with pyruvate

图式23. 水杨醛、丙二腈和苯乙酰叠氮的一锅三组分反应

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

图式24. 芳乙酰叠氮与丙烯腈类化合物的共轭加成反应

Scheme 24. Conjugate addition of phenacyl azides with acrylonitrile compounds

图式25. 苯乙酰叠氮与靛红亚乙基丙二腈的加成反应机理

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

图式26. 苯乙酰叠氮与烯基吲哚酮的共轭加成反应

Scheme 26. Conjugate addition of phenacyl azides with alkenyl oxindoles

图式27. 碱介导的苯乙酰叠氮与苯乙酰基溴的吡啶盐的微波辅助反应

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

图式28. 苯乙酰叠氮的多米诺序列合成吡咯化合物

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

图式29. DBU介导的苯乙酰叠氮与醛的偶联反应

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

图式30. 苯乙酰叠氮与炔的环加成反应

Scheme 30. Cycloaddition of phenacyl azides with alkyne

图式31. 苯乙酰叠氮与(碘乙炔基)苯的[3＋2]环加成反应

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

图式32. 苯乙酰叠氮与炔的1,3-偶极环加成反应

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

图式33. 苯乙酰叠氮与4,5-二(三甲基硅基)-1H-1,2,3-三唑的环加成反应

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

图式34. 芳乙酰叠氮与炔的1,3-偶极环加成反应

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

图式35. 苯乙酰叠氮与炔的1,3-偶极环加成反应

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

图式36. 芳乙酰叠氮通过氮杂Wittig反应合成噁唑

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

图式37. 苯乙酰叠氮通过氮杂Wittig反应合成噁唑

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

图式38. 芳乙酰叠氮通过氮杂Wittig反应合成吡咯

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

图式39. 芳乙酰叠氮的阴极还原反应过程

Scheme 39. Cathodic reduction process of phenacyl azides

图式40. 芳乙酰叠氮的自环化反应

Scheme 40. Self-cyclization of phenacyl azides

图式41. 苯乙酰叠氮的自由基链式反应

Scheme 41. Radical chain reactions of phenacyl azides

图式42. 芳乙酰叠氮的二聚化反应

Scheme 42. Dimerization of phenacyl azides

图式43. 芳乙酰叠氮的自环化反应

Scheme 43. Self-cyclization of phenacyl azides

图式44. 苯乙酰叠氮的Vilsmeier反应

Scheme 44. Vilsmeier reaction of phenacyl azides

图式45. 苯乙酰叠氮合成三取代吡咯

Scheme 45. Synthesis of trisubstituted pyrrole from phenacyl azides

图式46. 苯乙酰叠氮的热重排

Scheme 46. Thermal rearrangement of phenacyl azides

图式47. 芳乙酰叠氮与邻苯二胺的环化反应

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

图式48. 碘促进的芳乙酰叠氮与苯甲酰肼的缩合环化反应

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

图式49. 苯乙酰叠氮的脱氮环加成反应

Scheme 49. Denitrogenation and cycloaddition of phenacyl azides

图式50. 芳乙酰叠氮与丁炔二酸二酯的脱氮环化反应机理

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

图式51. Cu(OAc)2-Et3N介导芳乙酰叠氮的氧化偶联反应

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

图式52. 碱介导芳乙酰叠氮与马来酰亚胺的环加成反应机理

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

图式53. 铜催化苯乙酰叠氮与邻氨基苯乙酮环化反应机理

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

图式54. 芳乙酰叠氮的脱氮重排反应

Scheme 54. Denitrogenation and arrangement of phenacyl azides

图式55. 苯乙酰叠氮的脱氮环化反应

Scheme 55. Denitrogenation and cyclization of phenacyl azides

图式56. 芳乙酰叠氮的分子间Mannich反应

Scheme 56. Intermolecular Mannich reaction of phenacyl azides

图式57. 苯乙酰叠氮的脱氮[4＋2]环加成反应机理

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

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