含双杂原子苯并[d]五元杂环硫醚类化合物的合成研究进展

doi:10.6023/cjoc202306003

摘要/Abstract

具有双杂原子的苯并[d]噻唑/噁唑/咪唑等苯并[d]五元杂环硫醚结构广泛存在于许多药物分子和天然产物分子中, 其衍生物具有抗菌、抗病毒及抗肿瘤等广泛的生物活性, 同时也是有机合成的重要中间体及药物合成的结构单元. 因此, 苯并[d]噻唑/噁唑/咪唑硫醚化合物在医药、材料等领域具有极大的应用价值. 其合成方法的研究也成为当前的研究热点之一. 综述了近年来具有双杂原子的苯并[d]五元杂环硫醚类化合物的合成方法及其生物活性研究进展, 并对其部分反应机理做了相应的阐述.

关键词: 苯并[d]噻唑硫醚, 苯并[d]噁唑硫醚, 苯并[d]咪唑硫醚, C—S键形成, 研究进展

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

引用此文

贾小英, 普佳霞, 韩丽荣, 李清寒. 含双杂原子苯并[d]五元杂环硫醚类化合物的合成研究进展[J]. 有机化学, 2024, 44(1): 18-40.

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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图/表 75

图1. 具有生物活性的苯并[d]五元杂环硫醚化合物

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

图式1. 铜催化碘苯与硫化物反应制备苯并[d]噻唑硫醚化合物

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

图式2. 铜催化硫化物与亲核试剂反应制备苯并[d]噻唑硫醚化合物

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

图式3. 铜催化苯并[d]噁唑化合物与二苯二硫醚反应制备苯并[d]噁唑硫醚化合物

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

图式4. 铜催化苯并[d]噁唑化合物与二苯基二硫醚的可能反应机理

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

图式5. 铜催化苯并[d]噻唑与硫酚反应制备苯并[d]噻唑硫醚化合物

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

图式6. 铜催化硼酸与2-巯基苯并[d]噻唑制备苯并[d]噻唑硫醚

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

图式7. 铜催化苯并[d]噻唑与硫及卤苯反应制备苯并[d]噻唑硫醚化合物

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

图式8. 铜催化苯并[d]噻唑与硫及卤苯反应的可能反应机理

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

图式9. 铜催化杂芳基硫醇与(杂)芳基卤化物反应制备苯并[d]五元杂环硫醚化合物

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

图式10. 铜催化硼酸与2-巯基苯并[d]咪唑反应制备苯并[d]咪唑硫醚化合物

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

图式11. 铜催化硼酸与2-巯基苯并[d]咪唑反应的可能反应机理

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

图式12. 铜催化硼酸与N-硫杂芳基丁二酰亚胺反应制备苯并[d]五元杂环硫醚化合物

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

图式13. 铜催化硼酸与N-硫杂芳基丁二酰亚胺的可能反应机理循环图

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

图式14. 铜催化2-碘苯胺、二硫化碳与硫酚制备苯并[d]噻唑硫醚化合物

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

图式15. 铜催化2-碘苯胺、二硫化碳与硫酚反应的可能反应机理

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

图式16. 铜催化苯并[d]噻唑/噁唑与硫醇反应制备苯并[d]噻唑/噁唑硫醚化合物

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

图式17. 铜催化2-巯基苯并[d]噻唑与碘苯反应制备苯并[d]噻唑硫醚化合物

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

图式18. 铜催化2-巯基苯并[d]噻唑与碘苯反应的可能机理循环图

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

图式19. 铜催化2-巯基苯并[d]噻唑与芳基卤化物反应制备苯并[d]噻唑硫醚化合物

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

图式20. 铜催化苯并[d]五元杂环化合物与二苯基二硫醚反应制备苯并[d]五元杂环硫醚化合物

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

图式21. 苯并[d]五元杂环化合物与二苯基二硫醚的反应机理

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

图式22. 微波作用下铜催化2-巯基苯并[d]噻唑与碘苯反应制备苯并[d]五元杂环硫醚化合物

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

图式23. 微波作用下铜催化2-巯基苯并[d]噻唑与碘苯反应的可能机理

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

图式24. 可见光促进铜催化苯并[d]噻唑与硫及卤苯反应制备苯并[d]噻唑硫醚化合物

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

图式25. 纳米铜催化二硫化物与苯并[d]噻唑反应制备苯并[d]五元硫醚化合物

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

图式26. 纳米铜催化二硫化物与苯并[d]噻唑反应的可能机理

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

图式27. 纳米CuFe2O4催化2-巯基苯并[d]噻唑与芳基碘反应制备苯并[d]噻唑硫醚化合物

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

图式28. 镍催化2-巯基苯并[d]噻唑/噁唑与芳基铝反应制备苯并[d]噻唑/噁唑硫醚化合物

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

图式29. 镍催化2-巯基苯并[d]噻唑/噁唑与芳基铝反应的可能机理

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

图式30. 纳米Fe3O4催化二硫化物与苯并[d]噻唑反应制备苯并[d]噻唑硫醚化合物

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

图式31. NCS作用下硫酚与N-硫酰丁二酰亚胺及格氏试剂反应制备杂芳基硫醚化合物

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

图式32. NCS作用下有机锌试剂与巯基苯并[d]噻唑/噁唑反应制备苯并[d]噻唑/噁唑硫醚化合物

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

图式33. 浓硫酸或AlCl3作用下芳香醇与巯基苯并[d]噻唑/噁唑反应制备苯并[d]噻唑/噁唑硫醚化合物

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

图式34. 2-巯基苯并[d]五元杂环与芳基化合物的氧化交叉脱氢偶联反应

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

图式35. 2-巯基苯并[d]五元杂环与芳基化合物的交叉偶联反应的可能机理循环图

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

图式36. 2-巯基苯并[d]噻唑与内消旋环氧乙烷化合物的开环反应

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

图式37. 酸性离子液体[BsCtP][OTf]催化2-巯基苯并[d]噻唑/噁唑与芳香醇的偶联反应

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

图式38. 醇硫基化的可能机理

Scheme 38. Proposed mechanism for the thiolation of alcohols

图式39. TFA催化2-巯基苯并[d]噻唑与吲哚衍生物的交叉脱氢偶联反应

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

图式40. 2-烷硫基苯并[d]咪唑类化合物的合成

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

图式41. 2-巯基苯并[d]噁唑与卤代烃反应合成苯并[d]噁唑硫醚化合物

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

图式42. NaOMe催化2-巯基苯并[d]噻唑/噁唑/咪唑与2-溴-5硝基噻唑的交叉偶联

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

图式43. 微波辅助合成苯并[d]咪唑硫醚

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

图式44. DBU促进2-氨基苯并[d]噻唑/噁唑与二硫化碳及溴代烃一锅合成苯并[d]噻唑/噁唑硫醚化合物

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

图式45. DBU促进2-氨基苯唑与二硫化碳及溴代烃一锅合成苯唑硫醚的可能反应机理

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

图式46. 可见光促进碱催化2-巯基苯并[d]噻唑与碘苯反应制备苯并[d]噻唑硫醚化合物

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

图式47. 可见光促进玫瑰红催化苯并[d]噻唑/噁唑/咪唑与芳基肼反应制备苯并[d]噻唑/噁唑/咪唑硫醚化合物

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

图式48. 可见光促进玫瑰红催化苯并唑与芳基肼反应的可能机理循环图

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

图式49. 无过渡金属条件下一锅法合成苯并唑硫醚

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

图式50. 无过渡金属条件下一锅法合成苯并唑硫醚的可能反应机理

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

图式51. 不对称氧化制备R-对映异构体的埃索美拉唑

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

图式52. 2-苄硫基取代苯并[d]噻唑/噁唑类化合物的合成

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

图式53. n-BuLi催化2-巯基苯并[d]噁唑与二苯基溴甲烷的交叉偶联

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

图式54. 2-(苄硫基)-1H-苯并[d]咪唑类化合物的合成

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

图式55. 3-(苯并[d]噻唑-2-基硫基)-5-氯-4H-1,2,6-噻二嗪-4-酮的合成

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

图式56. 无金属无碱条件下的一锅两步法合成吡啶-2-甲基硫醚

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

图式57. 奥美拉唑硫化物的合成

Scheme 57. Synthesis of omeprazole sulfide

图式58. 雷贝拉唑硫化物的合成

Scheme 58. Synthesis of ribeprazole sulfide

图式59. 吡啶-2-甲硫醚的合成机理

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

图式60. 2-巯基苯并[d]噻唑与二芳基碘盐制备苯并[d]噻唑硫醚化合物

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

图式61. 分子内含有二硫代苯并[d]噻唑官能团的硼酸酯衍生物添加剂BTSB的合成

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

图式62. 2-巯基苯并[d]咪唑与二苯基碘三氟甲磺酸盐反应合成2-苯硫基苯并[d]咪唑

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

图式63. 2-巯基苯并[d]咪唑与二苯基碘三氟甲磺酸盐反应的可能机理

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

图式64. 2-巯基苯并[d]五元杂环与二芳基碘盐反应制备苯并[d]五元杂环硫醚化合物

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

图式65. HFIP促进2-氯苯并[d]噻唑与硫酚的亲核取代反应

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

图式66. HFIP促进2-氯苯并[d]噻唑与硫酚的亲核取代反应的可能机理

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

图式67. 组织蛋白酶D衍生物的合成

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%.

图式68. 5(6)-取代-(1H-苯并[d]咪唑-2-硫基)乙酸哌嗪衍生物的合成

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

图式69. 苯并[d]噻唑硫醚类化合物的合成

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

图式70. 具有1,3,4-噁唑结构的苯并[d]咪唑硫醚类化合物的合成

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

图式71. 苯并[d]咪唑硫醚衍生物的合成

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

图式72. 苯并[d]咪唑硫醚类化合物的合成

Scheme 72. Synthesis of benzo[d]Imidazole sulfides

图式73. 1,2,4-三唑酮的苯并噁唑衍生物的合成

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

图式74. 新型苯并[d]噁唑衍生物的合成

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

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