Recent Advances in the Synthesis of Fused Heterocyclic Compounds and Their Antitumor Activities

doi:10.6023/cjoc202211046

Abstract

The unique physicochemical properties invest fused heterocyclic compounds with wide applications in the synthesis of natural products, drugs, superconducting materials, energy storage materials, polymer materials, organic dyes, etc. In recent years, the rapid development of transition metal-catalyzed reactions of unsaturated hydrocarbons has developed rapidly. Owing to the advantages of high step- and atom-economy, easy availability of raw starting materials, and efficient construction of carbon-carbon bonds or/and carbon-hetero bonds, it is a vital way to synthesize fused heterocyclic compounds. Herein, the recent progress on the reaction development of transition metal-catalyzed cyclizations involving unsaturated hydrocarbons for the synthesis of fused heterocyclic compounds including benzofurans, indoles, quinolines in the last five years has been summarized, as well as their applications in the field of medicinal chemistry with antitumor activities.

Key words: unsaturated hydrocarbons, transition metal-catalysis, fused heterocyclic compounds, antitumor activity

Cite this article

Kanghui Duan, Junlong Tang, Wanqing Wu. Recent Advances in the Synthesis of Fused Heterocyclic Compounds and Their Antitumor Activities[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 826-854.

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Fig. & Tab. 76

Figure 1. Top 200 drugs with fused heterocyclic structure by sales in 2020

Figure 2. Benzofurans with biological activity

Scheme 1. Silver-catalyzed cyclization of 1,6-enyne with sodium sulfonate

Scheme 2. Palladium-catalyzed tandem cyclization reactions

Scheme 3. Palladium-catalyzed cyclization of aryl iodides and alkynes

Scheme 4. Nickel-catalyzed synthesis of 3-enylbenzofuran derivatives

Scheme 5. Nickel-catalyzed 1,2-carboamination of unactivated olefins

Scheme 6. Nickel-catalyzed asymmetric Heck cyclization of alkenyl ethers with cyclic vinyl ethylene carbonates

Scheme 7. Palladium-catalyzed cascade cyclization of alkenyl ethers with alkynyl oxime ethers

Scheme 8. Iridium-catalyzed synthesis of polyfunctional furans

Scheme 9. Indole compounds with biological activity

Scheme 10. Palladium-catalyzed asymmetric Heck cyclization of N-aryl acrylamides

Scheme 11. Palladium-catalyzed intramolecular oxidative aminoarylation of olefins

Scheme 12. Silver-catalyzed asymmetric [3+3] cyclization of azoimides

Scheme 13. Copper/N,O-ligand and BF3?Et2O-catalyzed Michael addition/aza-Friedel-Crafts reaction

Scheme 14. Nickel-catalyzed domino Heck cyclization reaction

Scheme 15. Iron-catalyzed reductive cyclization by hydromagnesiation

Scheme 16. Palladium-catalyzed asymmetric cyclization of aniline-tethered alkynyl cyclohexadienones

Scheme 17. Palladium-catalyzed synthesis of indole derivatives from alkynes

Scheme 18. Palladium-catalyzed synthesis of indoles bearing a chiral C2-aryl axis

Scheme 19. Palladium-catalyzed cyclization of o-iodoaryna- mide with 1,2-di-tert-butyldiaza-3-one

Scheme 20. Palladium-catalyzed cyclization of alkyne aryl iodide with secondary hydroxylamine

Scheme 21. Palladium-catalyzed cyclization of alkyne aryl iodide with tert-hydroxylamine

Scheme 22. Pd-catalyzed amino-cyclization and desymmetri- zing nitrile addition cascade reaction of alkyne-tethered malononitrile

Scheme 23. Palladium-catalyzed domino cyclization of alkyne-tethered nucleophiles

Scheme 24. Ruthenium-catalyzed cyclization of N-arylpyrazo- lone with alkyne

Scheme 25. Rhodium-catalyzed cyclization of N-alkylaniline with endoyne

Scheme 26. Rhodium-catalyzed cyclization of 1-aryl pyrazolidinone with alkynyl cyclobutanol

Scheme 27. Nickel- or copper-catalyzed cyclization for the synthesis of indole derivatives

Scheme 28. Gold-catalysed dearomative cascade cyclization

Scheme 29. Palladium-catalyzed Heck cyclization of o-halogenamide with o-ynylaniline

Scheme 30. Palladium-catalyzed cyclization of o-iodoaryna- mide with alkyne

Scheme 31. Biologically active benzothiophene and benzothiazole compounds

Scheme 32. Copper-catalyzed cross-coupling reactions

Scheme 33. Copper-catalyzed three-component tandem cyclization for the synthesis of benzothiazole

Scheme 34. Copper-catalyzed three-component tandem cyclization for the synthesis of bis-thiocyclic compounds

Scheme 35. Rhodium-catalyzed three-component tandem cyclization for the synthesis of benzothiophene

Scheme 36. Biologically active quinolines

Scheme 37. Ruthenium-catalyzed oxidative cyclization reactions

Scheme 38. Palladium-catalyzed carbocyclization of o-formylalynamide

Scheme 39. Zinc-catalyzed cyclization for the synthesis of 4-substituted quinolines

Scheme 40. Palladium-catalyzed cyclization of 2-azidophenyl- propynol

Scheme 41. Copper-catalyzed cyclization of arylonitrile and 2-ethynylaniline

Scheme 42. Copper-catalyzed intramolecular [4+2] cycloaddition reactions

Scheme 43. Copper-catalyzed selective cyclization of 2-aryl pyridine

Scheme 44. Gold-catalyzed 1,8-diyne isomerization reaction

Scheme 45. Silver-catalyzed tandem cyclization of o-alkynyl- aryimine with indole

Scheme 46. Palladium-catalyzed synthesis of benzofuran and indolin derivatives

Scheme 47. Rhodium-catalyzed conversion of azo-benzenes to indoles and indolines

Scheme 48. Palladium-catalyzed asymmetric tandem Heck/ Suzuki coupling reaction

Scheme 49. Palladium-catalyzed coupling-cyclization reactions of alkynes and 2-iodo derivatives

Scheme 50. Palladium-catalyzed three-component cascade cyclization reactions

Scheme 51. Palladium-catalyzed cascade cyclization of 1,6-enyne with arylboronic acid and ethyl difluoroiodoacetate

Scheme 52. Nickel-catalyzed cyclization of N-(2-bromophenyl)-N-acrylamide with trifluoromethylolefins

Scheme 53. Palladium-catalyzed domino cyclization of allyl ethers

Scheme 54. Silver-promoted cyclization of ene-yne-ketone with cyanoacetate

Scheme 55. Rhodium-catalyzed undirected C—H activation reaction

Scheme 56. Nanopalladium-catalyzed tandem cyclization of o-iodobenzyltriazole with alkynes

Scheme 57. Copper-catalyzed asymmetric cyclization of diynes

Scheme 58. Copper-catalyzed asymmetric cyclization of azide enynes

Scheme 59. Palladium-catalyzed Heck cyclization reaction

Scheme 60. Ni-Al bimetallic-catalyzed acyclization of olefins

Figure 3. Antitumor agent with benzofuran structure

Figure 4. Antitumor agent with benzofuran structure

Figure 5. Antitumor agent with indole structure

Figure 6. Antitumor agent with indole structure

Figure 7. Antitumor agent with indole structure

Figure 8. Antitumor agent with indole structure

Figure 9. Antitumor agents with benzothiazole structure

Figure 10. Antitumor agents with benzothiazole structure

Figure 11. Antitumor agents with benzothiazole structure

Figure 12. Antitumor agents with benzothiazole structure

Figure 13. Antitumor agents with benzothiazole structure

Figure 14. Antitumor agent with quinoline structure

Figure 15. Antitumor agent with quinoline structure

Figure 16. Antitumor agent with quinoline structure

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