氮杂螺[4.5]三烯酮衍生物的合成研究进展

doi:10.6023/cjoc202304004

摘要/Abstract

氮杂螺[4.5]三烯酮衍生物作为一种广泛存在于天然产物和活性药物成分中的重要结构单元, 由于其具有优异的结构性能和生物活性, 在有机合成领域得到了广泛应用. 近年来, 通过过渡金属参与、可见光促进、无过渡金属参与和电化学促进等几种方法, 高效构建了含各种官能团的氮杂螺[4.5]三烯酮衍生物. 综述了氮杂螺[4.5]三烯酮合成的最新研究进展, 并对代表性底物及反应机理进行了归纳和讨论.

关键词: 氮杂螺[4.5]三烯酮, 去芳构化, 原位环化, N-芳基丙炔酰胺

As one of the most important structural motifs in natural compounds and active pharmaceutical ingredients, aza- spiro[4.5]trienones derivatives have been widely used in the field of organic synthesis due to their excellent structural properties and biological activities. In recent years, several methods, such as transition metal involvement, visible light promotion, transition metal-free involvement and electrochemical promotion, have been used to efficiently construct various functional groups of azaspiro[4.5]trienones. The recent advances in the synthesis of azaspiro[4.5]trienones are reviewed, and the representative substrates and reaction mechanisms are summarized and discussed.

Key words: azaspiro[4.5]trienone, dearomatization, ipso-cyclization, N-alkylpropiolamide

引用此文

唐菁, 罗文坤, 周俊. 氮杂螺[4.5]三烯酮衍生物的合成研究进展[J]. 有机化学, 2023, 43(9): 3006-3034.

Jing Tang, Wenkun Luo, Jun Zhou. Advances in the Synthesis of Azaspiro[4.5]trienones[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3006-3034.

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图/表 59

图1. 具有代表性生物活性的氮杂螺[4.5]三烯酮衍生物

Figure 1. Representative biologically active azaspiro[4.5]trienones

图式1. 铜催化活化炔烃的氧化原位环化

Scheme 1. Copper-catalyzed oxidative ipso-cyclization of activated alkynes

图式2. 铜催化N-芳基丙炔酰胺的自由基串联环化反应

Scheme 2. Copper-catalyzed radical tandem cyclization of N-arylpropiolamides

图式3. 铜催化N-(对甲氧基芳基)丙炔酰胺、二硫醚和水的氧化原位环化反应

Scheme 3. Copper-catalyzed oxidative ipso-cyclization of N-(p-methoxyaryl)propiolamides with disulfides and H2O

图式4. 铜催化丙炔酰胺和烷烃的氧化原位环化反应

Scheme 4. Copper-catalyzed oxidative ipso-cyclization of propiolamides with alkanes

图式5. 铜催化丙炔酰胺和硅烷的氧化原位环化反应

Scheme 5. Copper-catalyzed oxidative ipso-cyclization of propiolamides with silane

图式6. 铜催化硝基芳烃衍生物的去芳基化脱硝反应

Scheme 6. Copper-catalyzed dearomatization and denitration of nitroaromatic derivatives

图式7. 铜催化原位环化反应

Scheme 7. Copper-catalyzed ipso-cyclization

图式8. 铁催化的氧化原位环化反应

Scheme 8. Iron-catalyzed oxidative ipso-cyclization

图式9. 亲电硒氰环化和脱芳构化螺环化反应

Scheme 9. Electrophilic selenocyanogen cyclization and dearomative spirocyclization

图式10. 银催化丙炔酰胺和磷酸的氧化原位环化反应

Scheme 10. Silver-catalyzed oxidative ipso-cyclization of propiolamides with phosphoric acid

图式11. 银催化丙炔酰胺和硫酚的氧化原位环化反应

Scheme 11. Silver-catalyzed oxidative ipso-cyclization of propiolamides with thiophenol

图式12. 银介导N-芳基丙炔酰胺的去芳构化反应

Scheme 12. Silver-mediated dearomatization of N-aryl propiolamides

图式13. N-芳基丙炔酰胺的脱芳香螺环化反应

Scheme 13. Dearomatization spirocyclization of N-aryl propiolamides

图式14. N-芳基丙炔酰胺的氧化螺环化反应

Scheme 14. Oxidative spirocyclization of N-aryl propiolamides

图式15. 银介导N-芳基丙炔酰胺的去芳构化反

Scheme 15. Silver-mediated dearomatization of N-aryl propiolamides

图式16. 银催化N-芳基丙炔酰胺的去芳构化反

Scheme 16. Silver-catalyzed dearomatization of N-aryl propiolamides

图式17. 镍促进的氧化原位环化反应

Scheme 17. Nickl-promoted oxidative ipso-cyclization

图式18. ZnBr2介导丙炔酰胺的去芳构化反应

Scheme 18. ZnBr2-mediated dearomatization of propiolamides

图式19. 钯催化的脱芳香化[2+2+1]碳环化反应

Scheme 19. Palladium-catalyzed dearomatizing [2+2+1] carbocyclization

图式20. 铝催化N-(对氟芳基)丙炔酰胺的去芳构化反应

Scheme 20. AlCl3-catalyzed dearomatization of N-para-fluoroaryl propiolamides

图式21. AlCl3催丙炔酰胺的去芳构化反应

Scheme 21. AlCl3-catalyzed dearomatization of propiolamides

图式22. 可见光促进N-芳基丙炔酰胺氧化环化反应

Scheme 22. Visible light-induced oxidative cyclization reaction of N-aryl propiolamides

图式23. 可见光促进N-芳基丙炔酰胺与硫醇的氧化环化反应

Scheme 23. Visible light-induced oxidative cyclization reaction of N-aryl propiolamides with mercaptan

图式24. 丙炔酰胺与二硒化合物的氧化环化反应

Scheme 24. Oxidative cyclization reaction of propiolamides with diselenid compounds

图式25. N-芳基丙炔酰胺与NH4SCN的自由基加成/环化反应

Scheme 25. Radical addition/cyclization reaction of N-aryl acrylamides with NH4SCN

图式26. 可见光促进N-芳基丙炔酰胺的卤代螺环化反应

Scheme 26. Visible light-induced halogenated spirocyclization reaction of N-aryl acrylamides

图式27. 丙炔酰胺与硫酚的自由基加成/环化反应

Scheme 27. Radical addition/cyclization reaction of propiolamides with thiophenol

图式28. 丙炔酰胺与叔丁酸三乙酯的自由基加成/环化反应

Scheme 28. Radical addition/cyclization reaction of propiolamides with triethyl tert-butyrate

图式29. N-芳基丙炔酰胺与二苯基膦的自由基加成/环化反应

Scheme 29. Radical addition/cyclization reaction of N-aryl propiolamides with diphenylphosphine

图式30. 3-溴氮杂螺[4.5]三烯酮衍生物的合成

Scheme 30. Synthesis of 3-bromoazaspiro[4.5]trienones

图式31. 可见光促进脱羧基芳基化反应

Scheme 31. Visible light-induced decarboxylation arylation

图式32. 可见光促进脱羧基芳基化反应

Scheme 32. Visible light-induced decarboxylation arylation

图式33. 可见光促进二氟烷基螺环化反应

Scheme 33. Visible light-induced difluoroalkyl spirocyclization

图式34. 可见光诱导原位二氟甲基化反应

Scheme 34. Visible light-induced ipso-difluoromethylation

图式35. 可见光诱导原位环化反应

Scheme 35. Visible light-induced ipso-cyclization

图式36. 可见光诱导邻近双官能团化反应

Scheme 36. Visible light-induced vicinal difunctionalization

图式37. 可见光介导丙炔酰胺的原位环化反应

Scheme 37. Visible light-mediated ipso-cyclization of propiolamides

图式38. 可见光介导活化炔烃的原位环化反应

Scheme 38. Visible light-mediated ipso-cyclization of activated alkynes

图式39. 可见光介导N-芳基丙炔酰胺与芳胺的氧化环化反应

Scheme 39. Visible light-induced oxidative cyclization reaction of N-aryl propiolamides with arylamine

图式40. 可见光介导二芳基烷基酰胺螺环化反应

Scheme 40. Visible light-induced spirocyclizative reaction of diaryl alkyl amides

图式41. 可见光介导炔烃与酰基肟酯的酰化/环化反应

Scheme 41. Visible light-induced acylation/cyclization reaction of alkynes with acyl oxime esters

图式42. 分子内原位环化反应合成氮杂螺[4.5]三烯酮

Scheme 42. Intramolecular ipso-cyclization to synthesize azaspiro[4.5]trione

图式43. 无过渡金属条件下炔和醛的原位环化反应

Scheme 43. Metal-free oxidative ipso-cyclization of alkynes with aldehyde

图式44. 炔烃的硝化螺环化反应

Scheme 44. Nitrative spirocyclization of alkynes

图式45. 无金属的直接氧化螺环化反应

Scheme 45. Metal-free direct oxidative spirocyclization

图式46. Ugi 4CC/亲电原位环化反应

Scheme 46. Ugi 4CC/electrophilic ipso-cyclization

图式47. 酸性环境下的分子内原位环化反应

Scheme 47. ispo-Cyclization under acidic conditions

图式48. Na2S2O8促进N-芳基丙炔酰胺的自由基环化

Scheme 48. Na2S2O8-promoted radical cyclization of N-aryl propiolamides

图式49. 酸引发的氧化级联反应

Scheme 49. Acid-triggereed oxidative cascade reaction

图式50. 硒促进的亲电环化反应

Scheme 50. Selenium-promoted electrophilic cyclization

图式51. 3-有机硒基氮杂螺环化合物的合成策略

Scheme 51. Synthetic strategy of 3-organic selenium azospiric compounds

图式52. 丙炔酰胺的串联环化反应

Scheme 52. Cascade annulation of propiolamides

图式53. 丙炔酰胺与α-氧代羧酸的无金属螺环化反应

Scheme 53. Metal-free spirocyclization of propiolamides with α-oxocarboxylatic acids

图式54. SOCl2介导3-甲硫基螺[4.5]三烯酮的合成

Scheme 54. SOCl2 mediated synthesis of 3-methylthiospiro[4.5]trienones

图式55. N-芳基丙炔酰胺的烷基化/原位环化反

Scheme 55. Alkylation/ipso-cyclization of N-arylpropiolamides

图式56. 电化学合成氮杂螺[4.5]三烯酮化合物

Scheme 56. Electrochemical synthesis of azaspiro[4.5]trienones

图式57. N-芳基丙炔酰胺电化学氧化卤化反应

Scheme 57. Electrochemical oxidative halogenation of N-arylpropiolamides

图式58. 3-卤代氮杂螺[4.5]三烯酮的合成

Scheme 58. Synthesis of 3-halozaspiro[4.5]trienones

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