喹啉和异喹啉衍生物合成方法研究进展

doi:10.6023/cjoc202502036

摘要/Abstract

喹啉和异喹啉环合成方法研究在医药和化工领域已逐渐占据重要地位, 其特殊杂环结构使其成为药物化学和有机化学领域中重要的先导化合物. 喹啉和异喹啉分子具有抗疟疾、抗阿尔兹海默症、抗肿瘤、抗高血压、抗氧化、抗菌等生物学活性. 综述了喹啉和异喹啉衍生物在药物化学和有机化学领域的重要意义, 进而系统阐述了近年来其在金属催化和非金属催化条件下的新型和改良的传统合成方法路线的研究进展, 包括过渡金属催化、光催化、微波催化等, 以得到不同取代或环合的喹啉或异喹啉化合物.

关键词: 喹啉, 异喹啉, 金属催化, 非金属催化, 合成

Synthesis methods of quinoline and isoquinoline rings have gradually occupied an important position in the field of medicine and chemical industry. Their special heterocyclic structures make them important lead compounds in medicinal chemistry and organic chemistry. Quinoline and isoquinoline molecules have anti-malaria, anti-Alzheimer’s disease, anti-tumor, anti-hypertension, anti-oxidation, antibacterial and other biological activities. The significance of quinoline and isoquinoline derivatives in the field of medicinal chemistry and organic chemistry is reviewed, and then the research progress of new and improved traditional synthesis methods, including transition metal catalysis, photocatalysis and microwave catalysis under the condition of metal and non-metal catalysis, in recent years is systematically reviewed, so as to obtain different substituted or cyclized quinoline or isoquinoline compounds.

Key words: quinoline, isoquinoline, metal catalysis, non-mteal catalysis, synthesis

引用此文

关丽萍, 林志琦, 方超华, 王秋实, 符志杨, 张斌. 喹啉和异喹啉衍生物合成方法研究进展[J]. 有机化学, 2025, 45(9): 3255-3288.

Liping Guan, Zhiqi Lin, Chaohua Fang, Qiushi Wang, Zhiyang Fu, Bin Zhang. Advances in Synthesis Methods of Quinoline and Isoquinoline Derivatives[J]. Chinese Journal of Organic Chemistry, 2025, 45(9): 3255-3288.

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图/表 65

图1. 喹啉及异喹啉衍生物的药理活性

Figure 1. Pharmacological activities of quinoline and isoquinoline derivatives

图式1. 含喹啉或异喹啉环的药物

Scheme 1. Drugs containing quinoline or isoquinoline rings

图式2. 苯胺合成喹啉的传统方法

Scheme 2. Traditional method of synthesis of quinoline from aniline

图式3. 苯胺衍生物合成喹啉的多种方法

Scheme 3. Multiple methods for synthesis of quinoline from aniline derivatives

图式4. 铱催化一锅法合成3-苯硫代喹啉衍生物

Scheme 4. One-pot synthesis of 3-phenylthioquinoline derivatives catalyzed by iridium

图式5. 铱催化的反应机理

Scheme 5. Reaction mechanism catalyzed by iridium

图式6. Pd催化合成喹啉衍生物

Scheme 6. Synthesis of quinoline derivatives catalyzed by Pd

图式7. Fe3O4-TDSN-Bi(III)催化合成喹啉衍生物

Scheme 7. Fe3O4-TDSN-Bi(III) catalyzed the synthesis of quinoline derivatives

图式8. Fe3O4-TDSN-Bi(III)催化反应的潜在机理

Scheme 8. Potential mechanism of Fe3O4-TDSN-Bi(III) catalyzed reaction

图式9. TiO2-Al2O3-ZrO2催化合成喹啉衍生物

Scheme 9. Synthesis of quinoline derivatives by TiO2-Al2O3- ZrO2 catalysis

图式10. (PCy3)2(CO)RuHCl催化合成喹啉衍生物

Scheme 10. Synthesis of quinoline derivatives catalyzed by (PCy3)2(CO)RuHCl

图式11. (PCy3)2(CO)RuHCl催化反应的潜在机理

Scheme 11. The potential mechanism of the reaction catalyzed by (PCy3)2(CO)RuHCl

图式12. Co(II)络合物催化环化合成2,3-二取代喹啉

Scheme 12. Co(II) complexes catalyzed the cyclization to form 2,3-disubstituted quinolines

图式13. AgOTf催化合成喹啉衍生物

Scheme 13. Synthesis of quinoline derivatives catalyzed by AgOTf

图式14. 钯络合物催化Heck反应合成喹啉

Scheme 14. Synthesis of quinoline by Heck reaction catalyzed by palladium complex

图式15. 金属Mn络合物催化合成喹啉衍生物

Scheme 15. Synthesis of quinoline derivatives catalyzed by metal Mn complex

图式16. ZnCl2催化合成取代芳基喹啉的friedlander型反应

Scheme 16. Synthesis of substituted quinoline by ZnCl2 catalyzed friedlander type reaction

图式17. 银催化完成喹啉衍生物的取代反应

Scheme 17. The substitution reaction of quinoline derivatives was catalyzed by Ag

图式18. Cu(I)催化生成喹啉取代异苯并呋喃衍生物

Scheme 18. Cu(I) catalyzed the formation of quinoline-substituted isobenzofuran derivatives

图式19. 钯催化Suzuki Miyaura反应合成芳基喹啉

Scheme 19. Synthesis of arylquinoline by Pd-catalyzed Suzuki Miyaura reaction

图式20. Cu(I)催化合成吡咯并喹啉二酮

Scheme 20. Copper(I) catalyzed synthesis of pyrrolo quinoline diones

图式21. 在Cu(OAc)2催化下合成喹啉

Scheme 21. Synthesis of quinoline catalyzed by Cu(OAc)2

图式22. Cu(OAc)2催化下的反应机理

Scheme 22. Reaction mechanism catalyzed by Cu(OAc)2

图式23. 在CuI催化下合成吡咯[2,3-b]喹啉衍生物

Scheme 23. Synthesis of pyrrole [2,3-b] quinoline derivatives catalyzed by CuI

图式24. DBU催化合成2-二氟甲基取代的喹啉

Scheme 24. DBU catalyzed the synthesis of 2-difluoromethyl-substituted quinoline

图式25. 由TMSCl介导的三组分喹啉合成反应

Scheme 25. Synthesis of three-component quinoline mediated by TMSCl

图式26. I2催化经D-A反应合成喹啉衍生物

Scheme 26. Synthesis of quinoline derivatives by iodine catalyzed D-A reaction

图式27. CF3SO3H介导下合成喹啉

Scheme 27. Synthesis of quinoline mediated by CF3SO3H

图式28. 三氟化硼甲醚合物(BF3•O(CH3)2)催化下合成喹啉

Scheme 28. Synthesis of quinoline by boron trifluoride methyl ether complex (BF3•O(CH3)2)

图式29. 由四氢吡咯催化通过[4＋2]环化合成喹啉

Scheme 29. Quinoline formed from tetrahydropyrrole by [4＋2] cyclization

图式30. 通过2-芳基喹啉的芳基化合成喹啉

Scheme 30. Synthesis of quinolines by arylation of 2-aryl quinolines

图式31. TBHP促进喹啉合成方法

Scheme 31. TBHP promoted methodology for the synthesis of quinolines

图式32. 合成异喹啉衍生物的传统方法

Scheme 32. Traditional methods for synthesizing isoquinoline derivatives

图式33. Ru(II)催化的C—H活化合成异喹啉

Scheme 33. Synthesis of isoquinoline by C—H activation catalyzed by Ru(II)

图式34. 铜(I)催反应合成异喹啉

Scheme 34. Synthesis of isoquinoline catalyzed by copper (I)

图式35. Ru催化合成异喹啉

Scheme 35. Synthesis of isoquinoline catalyzed by Ru

图式36. 碱金属盐促进[4＋2]环加成异喹啉衍生物

Scheme 36. Alkali metal salts promote [4＋2] cycloaddition to isoquinoline derivatives

图式37. 钴(III)催化合成异喹啉衍生物

Scheme 37. Synthesis of isoquinoline derivatives catalyzed by cobalt(III)

图式38. 银(I)催化环化合成异喹啉衍生物

Scheme 38. Ag(I) catalyzed cyclization to form isoquinoline derivatives

图式39. CuCl2催化合成异喹啉衍生物

Scheme 39. Synthesis of isoquinoline derivatives catalyzed by CuCl2

图式40. Ni催化合成异喹啉

Scheme 40. Synthesis of isoquinoline catalyzed by Ni

图式41. Rh (III)催化合成异喹啉衍生物

Scheme 41. Synthesis of isoquinoline derivatives catalyzed by Rh(III)

图式42. [RhCp*Cl2]2催化合成异喹啉衍生物

Scheme 42. Catalytic synthesis of isoquinoline derivatives using [RhCp*Cl2]2

图式43. Rh(III)催化合成N-取代的1-氨基异喹啉

Scheme 43. Synthesis of N-substituted 1-amino-isoquinoline catalyzed by Rh(III)

图式44. Rh催化环化合成1-烷氧基异喹啉衍生物

Scheme 44. Rh catalyzed cyclization to form 1-alkoxy isoquinoline derivatives

图式45. Cu催化合成多取代异喹啉

Scheme 45. Synthesis of polysubstituted isoquinoline catalyzed by Cu

图式46. Ir催化合成反式四氢异喹啉

Scheme 46. Synthesis of trans-tetrahydroisoquinoline catalyzed by Ir

图式47. Cu催化[2＋2＋1]环化合成异喹啉

Scheme 47. Cu catalyzed [2＋2＋1] cyclization to isoquinoline

图式48. Rh/Pd接力催化合成异喹啉

Scheme 48. Synthesis of isoquinoline by Rh/Pd relay catalysis

图式49. Rh(III)催化合成异喹啉衍生物

Scheme 49. Synthesis of isoquinoline derivatives catalyzed by Rh(III)

图式50. Cu催化合成吡咯并[2,1-a]异喹啉

Scheme 50. Synthesis of pyrrole and [2,1-a] isoquinoline catalyzed by Cu

图式51. CuCl2催化反应的潜在机理

Scheme 51. Potential mechanism of the CuCl₂-catalyzed reaction

图式52. DMP介导的异喹啉-1,3-二酮的合成

Scheme 52. Synthesis of isoquinolin-1, 3-dione mediated by DMP

图式53. 一种由DMP介导的异喹啉氧化偶联反应的潜在机理

Scheme 53. A plausible mechanism for the oxidative coupling reaction of isoquinoline mediated by DMP

图式54. 合成1-烷基/芳基/二烷基氨基取代的异喹啉

Scheme 54. Synthesis of 1-alkyl/aryl/dialkyl amino substituted isoquinoline

图式55. 磺酰化吲哚并[2,1-a]异喹啉的合成

Scheme 55. Synthesis of sulfonated indole [2,1-a]isoquinoline

图式56. 不同取代硝基异喹啉-1,3-二酮的合成方法

Scheme 56. Synthetic method of different substituted nitroisoquinolin-1,3-diketone

图式57. 1-酰化异喹啉衍生物的合成

Scheme 57. Synthesis of 1-acylated isoquinoline derivatives

图式58. 3-酮-异喹啉衍生物的合成

Scheme 58. Synthesis of 3-keto-isoquinoline derivatives

图式59. α-杂芳化反应合成多取代异喹啉的方法

Scheme 59. Method for synthesizing polysubstituted isoquinoline by α-heteroaromatization

图式60. 异喹啉衍生物的合成方法

Scheme 60. Synthesis method of isoquinoline derivatives

图式61. 3-芳基异喹啉的合成方法

Scheme 61. Synthesis method of 3-aryl isoquinoline

图式62. 微波催化异喹啉衍生物的合成

Scheme 62. Synthesis of isoquinoline derivatives catalyzed by microwave

图式63. Ru配合物催化异喹啉衍生物的合成

Scheme 63. Synthesis of isoquinoline derivatives catalyzed by Ru complexes

图式64. Ru配合物催化异喹啉衍生物的合成的潜在机理

Scheme 64. Potential mechanism for the synthesis of isoquinoline derivatives catalyzed by Ru complexes

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