Research Progress in the Synthesis of Benzo[d]pentamembered Heterocyclic Thioethers Containing Two Heteroatoms

doi:10.6023/cjoc202306003

Abstract

The thioether structure of benzo[d]penta-membered heterocycles with double heteroatoms, such as benzo[d] thiazole/oxazole/imidazole, widely exists in many drug molecules and natural product molecules. Its derivatives have extensive biological activities such as antibacterial, antiviral and anti-tumor, and are also important intermediates in organic synthesis and structural units in drug synthesis. Therefore, benzo[d]thiazole/oxazole/imidazole sulfide compounds have great application value in medicine, materials and other fields. The research of its synthesis method has also become one of the current research hotspots. The synthesis methods and biological activity research progress of benzo[d]five membered heterocyclic sulfide compounds with double heteroatoms in recent years are reviewed, and some of their reaction mechanisms are described.

Key words: benzo[d]thiazole sulfide, benzo[d]oxazole sulfide, benzo[d]imidazole sulfide, C—S bond formation, research progress

Cite this article

Xiaoying Jia, Jiaxia Pu, Lirong Han, Qinghan Li. Research Progress in the Synthesis of Benzo[d]pentamembered Heterocyclic Thioethers Containing Two Heteroatoms[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 18-40.

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Fig. & Tab. 75

Figure 1. Benzo[d]five-membered heterocyclic sulfide compounds with biological activity

Scheme 1. Preparation of benzo[d]thiazole sulfide by the reaction of iodobenzene and sulfide catalyzed by copper

Scheme 2. Preparation of benzo[d]thiazole thioethers by the reaction of sulfide with nucleophilic reagent catalyzed by copper

Scheme 3. Preparation of benzo[d]oxazole sulfide compounds by the reaction of benzo[d]oxazole compounds with diphenyl disulfide catalyzed by copper

Scheme 4. Possible mechanism of the reaction of benzo[d]oxazole with diphenyl disulfide catalyzed by copper

Scheme 5. Preparation of benzo[d]thiazole thioether by the reaction of benzo[d]thiazole and thiophenol catalyzed by copper

Scheme 6. Copper catalyzed synthesis of benzo[d]thiazole sulfide from boric acid and 2-mercaptobenzo[d]thiazole

Scheme 7. Synthesis of benzo[d]thiazole thioethers from benzo[d]thiazole, sulfur and aryl halides catalyzed by copper

Scheme 8. Possible reaction mechanism of copper catalyzed reaction of benzo[d]thiazole with sulfur and halobenzenes

Scheme 9. Preparation of benzo[d]five-membered heterocyclic sulfides from heteroaryl mercaptans and (hetero)aryl halides catalyzed by copper

Scheme 10. Preparation of benzo[d]imidazole sulfide from boric acid and 2-mercaptobenzo[d]imidazole catalyzed by copper

Scheme 11. Possible reaction mechanism of the reaction of boric acid and 2-mercaptobenzo[d]imidazole catalyzed by copper

Scheme 12. Copper-catalyzed reaction of boric acid with N-thiaaryl succinimide to prepare benzo[d]pentacyclic sulfides

Scheme 13. Possible reaction mechanism of the reaction of boric acid with N-thioaryl succinimide catalyzed by copper

Scheme 14. Preparation of benzo[d]thiazole sulfides from 2- iodoaniline, carbon disulfide and thiophenol catalyzed by copper

Scheme 15. Possible mechanism of the reaction of 2-iodo- aniline, carbon disulfide and thiophenol catalyzed by copper

Scheme 16. Preparation of benzo[d]thiazole thioethers by the reaction of benzo[d]thiazole/oxazole with mercaptan catalyzed by copper

Scheme 17. Copper-catalyzed reaction of 2-mercaptobenzo- [d]thiazole with iodobenzene to prepare benzo[d]thiazole sulfide

Scheme 18. Possible mechanism of the reaction of 2-mercapto- benzo[d]thiazole with iodobenzene catalyzed by copper

Scheme 19. Copper-catalyzed reaction of 2-mercaptobenzo- [d]thiazole with aryl halide to prepare benzo[d]thiazole sulfide

Scheme 20. Copper-catalyzed reaction of benzo[d]five- membered heterocyclic compounds with diphenyl disulfide to prepare benzo[d]five-membered heterocyclic sulfides

Scheme 21. Mechanism of the reaction of benzo[d]five-mem- bered heterocyclic compounds with diphenyl disulfides

Scheme 22. Preparation of benzo[d]pentacyclic thioethers from 2-mercaptobenzo[d]thiazole and iodobenzene catalyzed by copper under microwave irradiation

Scheme 23. Possible mechanism of the reaction of 2-mercapto- benzo[d]thiazole and iodobenzene catalyzed by copper under microwave irradiation

Scheme 24. Preparation of benzo[d]thiazole sulfide by the reaction of benzo[d]thiazole with sulfur and halobenzene catalyzed by copper under visible light

Scheme 25. Preparation of benzo[d]pentathioether compounds by the reaction of disulfide with benzo[d]thiazole catalyzed by copper nanoparticles

Scheme 26. Possible reaction mechanism of the reaction of disulfide with benzo[d]thiazole catalyzed by copper nanoparticles

Scheme 27. Synthesis of benzo[d]thiazole thioethers from 2-mercaptobenzo[d]thiazole and aryl iodide catalyzed by Cu- Fe2O4 nanoparticles

Scheme 28. Preparation of benzo[d]thiazole/oxazole thioethers by the reaction of 2-mercaptobenzo[d]thiazole/oxazole with aryl aluminums catalyzed by nickel

Scheme 29. Possible mechanism of the reaction of 2-mercapto- benzo[d]thiazole/oxazole with aryl aluminums catalyzed by nickel

Scheme 30. Preparation of benzo[d]thiazole sulfide by the reaction of disulfide with benzo[d]thiazole catalyzed by nano-Fe3O4

Scheme 31. Preparation of heteroaryl sulfide compounds from thiophenol, N-thiosuccinimide and Grignard reagent under the action of NCS

Scheme 32. Preparation of benzo[d]thiazole/oxazole thioether by organic zinc reagent and thiobenzo[d] thiazole/oxazole under the action of NCS

Scheme 33. Preparation of benzo[d]thiazole/oxazole sulfide from aromatic alcohol and mercaptobenzo[d]thiazole/oxazole under the treatment of concentrated sulfuric acid or AlCl3

Scheme 34. Oxidative cross dehydrogenation coupling reaction of 2-mercaptobenzo[d]five-membered heterocycles with aryl compounds

Scheme 35. Possible mechanism of coupling reaction of 2-mercaptobenzo[d]five-membered heterocycles with aryl compounds

Scheme 36. Ring opening reaction of 2-mercaptobenzo[d]thiazole with racemic ethylene oxide compound

Scheme 37. Coupling reaction of 2-mercaptobenzo[d]thiazole/oxazole with aromatic alcohol catalyzed by acidic ionic liquid [BsCtP]- [OTf]

Scheme 38. Proposed mechanism for the thiolation of alcohols

Scheme 39. TFA-catalyzed cross dehydrogenation coupling of 2-mercaptobenzo[d]thiazole with indole derivatives

Scheme 40. Synthesis of 2-alkylthiobenzo[d]imidazole compounds

Scheme 41. Synthesis of benzo[d]oxazolethioether by the reaction of 2-mercaptobenzo[d]oxazole with haloalkane

Scheme 42. Cross-coupling of 2-mercaptobenzo[d]thiazole/ oxazole/imidazole with 2-bromo-5-nitrothiazole catalyzed by NaOMe

Scheme 43. Microwave assisted synthesis of benzo[d]imidazole sulfide

Scheme 44. DBU promotes one pot synthesis of 2-aminobenzo[d]thiazole/oxazole with carbon disulfide and brominated hydrocarbons to benzo[d]thiazole/oxazole sulfide

Scheme 45. Possible reaction mechanism of DBU promoting the one pot synthesis of 2-aminobenzozole with carbon disulfide and brominated hydrocarbons to benzozole sulfide

Scheme 46. Preparation of benzo[d]thiazole thioether from 2-mercaptobenzo[d]thiazole and iodobenzene catalyzed by base under visible light

Scheme 47. Preparation of benzo[d]thiazole/oxazole/imidazole thioether by the reaction of benzo[d]thiazole/oxazole/imidazole and aryl hydrazine catalyzed by rose Bengal under visible light

Scheme 48. Possible mechanism of the reaction of benzo[d]zole and aryl hydrazine catalyzed by rose Bengal under visible light

Scheme 49. One-pot synthesis of thiobenzoazoles using transition-metal-free conditions

Scheme 50. Plausible mechanism of one-pot synthesis of thiobenzoazoles under transition-metal-free conditions

Scheme 51. Preparation of esomeprazole of R-enantiomer by asymmetric oxidation

Scheme 52. Synthesis of 2-benzylthio substituted benzo[d]- thiazole/oxazole compounds

Scheme 53. Cross-coupling of 2-mercaptobenzo[d]oxazole with diphenyl bromomethane catalyzed by n-BuLi

Scheme 54. Synthesis of 2-(benzylthio)-1H-benzo[d]imidazole compounds

Scheme 55. Synthesis of 3-(benzo[d]thiazol-2-ylthio)-5-chloro-4H-1,2,6-thiadiazin-4-one

Scheme 56. One pot two-step synthesis of pyridine-2-methylthioether under metal and alkali free conditions

Scheme 57. Synthesis of omeprazole sulfide

Scheme 58. Synthesis of ribeprazole sulfide

Scheme 59. Mechanism of the synthesis of pyridine-2-methylthioether

Scheme 60. Preparation of benzo[d]thiazole thioether from 2- mercaptobenzo[d]thiazole and diaryliodide salt

Scheme 61. Synthesis of borate ester derivative additive BTSB containing dithiobenzo[d]thiazole functional groups within the molecule

Scheme 62. Synthesis of 2-phenylthiobenzo[d]imidazole by the reaction of 2-mercaptobenzo[d]imidazole with diphenyliodotrifluoromethanesulfonate

Scheme 63. Possible mechanism of the reaction of 2-mercapto- benzo[d]imidazole with diphenyliodotrifluoromethanesulfonate

Scheme 64. Preparation of benzo[d]five-membered heterocyclic sulfide compounds by the reaction of 2-mercaptobenzo[d]five- membered heterocycles with diaryliodide salts

Scheme 65. HFIP promoted nucleophilic Substitution reaction of 2-chlorobenzo[d]thiazole using thiols

Scheme 66. Possible mechanism of HFIP promoting nucleophilic substitution reaction of 2-chlorobenzo[d]thiazole with thiophenol

Scheme 67. Synthesis of cathepsin D derivatives Reagents and conditions: (a) phthalic anhydride, toluene, reflux. (b) 2-carboxymethylbenzenesulfonylchloride, pyridine, cat. DMAP, 60 ℃, 82%; then NaOH, MeOH, water, r.t., 62%. (c) 3,5-dichlorobenzoyl chloride, toluene, 100 ℃, 22%. (d) 3,5-dicbloro-2-hydroxy benzenesulfonyl chloride, pyridine, 50 ℃, 10%.

Scheme 68. Synthesis of piperazine derivatives of 5(6)-substituted-(1H-benz[d]imidazol-2-ylthio)acetic acids

Scheme 69. Synthesis of benzo[d]thiazole sulfide compounds

Scheme 70. Synthesis of benzo[d]imidazole sulfides with 1,3,4-oxazole structure

Scheme 71. Synthesis of benzo[d]imidazole sulfide derivatives

Scheme 72. Synthesis of benzo[d]Imidazole sulfides

Scheme 73. Synthesis of benzoxazole derivatives of 1,2,4-tria- zolone

Scheme 74. Synthesis of novel benzo[d]oxazole derivatives

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