Advances in Synthesis Methods of Quinoline and Isoquinoline Derivatives

doi:10.6023/cjoc202502036

Abstract

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

Cite this article

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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Fig. & Tab. 65

Figure 1. Pharmacological activities of quinoline and isoquinoline derivatives

Scheme 1. Drugs containing quinoline or isoquinoline rings

Scheme 2. Traditional method of synthesis of quinoline from aniline

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

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

Scheme 5. Reaction mechanism catalyzed by iridium

Scheme 6. Synthesis of quinoline derivatives catalyzed by Pd

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

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

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

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

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

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

Scheme 13. Synthesis of quinoline derivatives catalyzed by AgOTf

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 27. Synthesis of quinoline mediated by CF3SO3H

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

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

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

Scheme 31. TBHP promoted methodology for the synthesis of quinolines

Scheme 32. Traditional methods for synthesizing isoquinoline derivatives

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

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

Scheme 35. Synthesis of isoquinoline catalyzed by Ru

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

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

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

Scheme 39. Synthesis of isoquinoline derivatives catalyzed by CuCl2

Scheme 40. Synthesis of isoquinoline catalyzed by Ni

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

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

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

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

Scheme 45. Synthesis of polysubstituted isoquinoline catalyzed by Cu

Scheme 46. Synthesis of trans-tetrahydroisoquinoline catalyzed by Ir

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

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

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

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

Scheme 51. Potential mechanism of the CuCl₂-catalyzed reaction

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

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

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

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

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

Scheme 57. Synthesis of 1-acylated isoquinoline derivatives

Scheme 58. Synthesis of 3-keto-isoquinoline derivatives

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

Scheme 60. Synthesis method of isoquinoline derivatives

Scheme 61. Synthesis method of 3-aryl isoquinoline

Scheme 62. Synthesis of isoquinoline derivatives catalyzed by microwave

Scheme 63. Synthesis of isoquinoline derivatives catalyzed by Ru complexes

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

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