2-取代苯并噻唑化合物的合成进展

doi:10.6023/cjoc202007036

摘要/Abstract

2-取代苯并噻唑在生物医药、材料科学等领域的应用和研究使其合成方法受到了广泛的关注. 在传统合成方法的研究基础之上, 单质硫介导的氧化还原反应和饱和化合物的脱氢芳构化反应等新方法的发展, 为苯并噻唑衍生物的合成提供更多可能. 此外, 近年来新型金属-有机骨架催化剂、组合离子液体/凝胶、超声以及微波辅助等的应用, 极大地丰富了苯并噻唑衍生物的合成方式. 综述了近年来2-取代苯并噻唑的合成方法.

关键词: 2-取代苯并噻唑, 缩合, 脱氢, 氧化还原, 芳基化, 偶联环化

The application and research of 2-substituted benzothiazoles in biomedicine, materials science and other fields have made their synthetic methods widely concerned. Based on the research of traditional synthetic methods, the development of new methods such as elemental sulfur-mediated redox reaction and dehydroaromatization of saturated compounds could provide more possibilities for the synthesis of benzothiazole derivatives. In addition, the application of new metal-organic framework catalysts, combined ionic liquids/gels, ultrasound and microwave assist in recent years have greatly enriched the synthesis of benzothiazole derivatives. The synthetic method of 2-substituted benzothiazoles in recent years is analyzed.

Key words: 2-substituted benzothiazole, condensation, dehydrogenation, redox, arylation, coupling cyclization

引用此文

张俊, 刘雅菲, 张育榕, 呼亮, 韩世清. 2-取代苯并噻唑化合物的合成进展[J]. 有机化学, 2021, 41(3): 1053-1071.

Jun Zhang, Yafei Liu, Yurong Zhang, Liang Hu, Shiqing Han. Progress in Synthesis of 2-Substituted Benzothiazole Compounds[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1053-1071.

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图/表 50

图式1. 2-氨基苯硫酚与醛的反应机理

Scheme 1. Reaction mechanism of 2-aminothiophenol with aldehydes

图式2. 高活性催化剂催化2-取代苯并噻唑的合成

Scheme 2. Synthesis of 2-substituted benzothiazoles catalyzed by highly active catalysts

图式3. 非均相催化2-氨基苯硫酚与醛的反应

Scheme 3. Heterogeneous catalytic reaction of 2-aminothio- phenols with aldehydes

图式4. 邻位硼酸介导的点击环化反应

Scheme 4. Orthoboric acids mediated click cyclization

图式5. 可见光介导2-取代苯并噻唑的合成

Scheme 5. Visible light-mediated synthesis of 2-substituted benzothiazoles

图式6. 2-氨基苯硫酚与醛的缩合反应

Scheme 6. Condensation of 2-aminothiophenols with aldehydes

图式7. 酸催化2-氨基苯硫酚和β-二酮的反应

Scheme 7. Acid catalyzed reaction of 2-aminothiophenols with β-diketones

图式8. 离子-凝胶催化2-氨基苯硫酚和芳基酮的反应

Scheme 8. Reaction of 2-aminothiophenol and aryl ketones catalyzed by ion-gel

图式9. 金属-有机骨架催化2-苯基苯并噻唑的合成

Scheme 9. Synthesis of 2-phenylbenzothiazole catalyzed by metal-organic frameworks

图式10. 电化学介导的脱羧偶联反应

Scheme 10. Electrochemically mediated decarboxylation coupling reaction

图式11. 2-氨基苯硫酚与酮酸/酮酸盐的脱酸环化反应

Scheme 11. Deacidification cyclization of 2-aminothiophenols with ketoacids/ketoacid salts

图式12. 亚磷酸催化2-取代苯并噻唑的合成

Scheme 12. Synthesis of 2-substituted benzothiazoles catalyzed by phosphorous acid

图式13. 2-氨基苯硫酚和苯甲酸酐缩合反应

Scheme 13. Condensation reaction of 2-aminothiophenol and benzoic anhydride

图式14. 2,2'-二氨基二苯二硫醚的裂解合成苯并噻唑

Scheme 14. Synthesis of benzothiazole by cleavage of 2,2'-disulfanediyldianiline

图式15. 非金属催化2-取代苯并噻唑的合成

Scheme 15. Synthesis of 2-substituted benzothiazoles catalyzed by non-metal

图式16. 2-氨基苯硫酚和芳基苄胺的氧化环化反应

Scheme 16. Oxidative cyclization of 2-aminothiophenols with arylbenzylamines

图式17. 2-氨基苯硫酚和苄基胺的反应机理

Scheme 17. Reaction mechanism of 2-aminothiophenol with benzylamine

图式18. CBr4催化2-氨基苯硫酚和N-甲基硫酰胺的反应

Scheme 18. Reaction of 2-aminothiophenols with N-methylthio- amides catalyzed by CBr4

图式19. 过渡金属催化环化合成2-取代苯并噻唑

Scheme 19. Synthesis of 2-substituted benzothiazoles by transition metals catalyzed cyclization

图式20. 2-氨基苯硫酚和醇的缩合反应

Scheme 20. Condensation of 2-aminothiophenols and alcohols

图式21. Na2CO3介导2-氨基苯硫酚和硫醇的反应

Scheme 21. Na2CO3 mediated reaction of 2-aminothiophenol with mercaptans

图式22. 2,3-二氢苯并噻唑的脱氢反应

Scheme 22. Dehydrogenation of 2,3-dihydrobenzothiazoles

图式23. 脱氢芳构化合成2-取代苯并噻唑

Scheme 23. Synthesis of 2-substituted benzothiazoles by dehydroaomatization

图式24. 硫介导的邻氯硝基苯与苄胺的氧化还原缩合反应

Scheme 24. Sulfur mediated redox condensation of o-chloro- nitrobenzenes and benzylamines

图式25. Fe/S催化芳基乙酸与硝基芳烃的脱羧反应

Scheme 25. Fe/S catalyzed decarboxylation of arylacetic acids with nitroarenes

图式26. 硫介导的季铵盐和邻碘苯胺的串联环化反应

Scheme 26. Sulfur mediated tandem cyclization of quaternary ammonium salts and o-iodoanilines

图式27. 硫介导的邻氯硝基芳烃与芳基乙酸的脱羧反应

Scheme 27. Sulfur mediated decarboxylation of o-chloronitroarenes and arylacetic acids

图式28. 硫介导的邻氯硝基苯和苯甲醛的氧化还原缩合反应

Scheme 28. Sulfur mediated redox condensation of o-chloronitrobenzenes with benzaldehydes

图式29. 醇、邻溴硝基苯和硫脲的偶联反应

Scheme 29. Coupling of alcohols, o-bromonitrobenzenes and thiourea

图式30. 硫介导的2-氨基苯硫酚和芳基乙炔或苯乙烯的氧化环化反应

Scheme 30. Sulfur mediated oxidative cyclization of 2-aminothiophenols with arylacetylenes or styrenes

图式31. NH4I介导的芳胺、苯乙烯/芳基乙炔和元素硫的串联环化反应

Scheme 31. NH4I mediated tandem cyclization of arylamines, styrenes / arylacetylenes and elemental sulfur

图式32. 铜盐催化2-取代苯并噻唑的选择性构建

Scheme 32. Selective construction of 2-substituted benzothiazoles catalyzed by copper salts

图式33. FeCl3催化的硝基芳烃、醇和元素硫的串联环化

Scheme 33. Tandem cyclization of nitroaromatics, alcohols and elemental sulfur catalyzed by FeCl3

图式34. TBHP/KI介导苯胺、醚和元素硫的偶联反应

Scheme 34. Coupling of anilines,ethers,and elemental sulfur mediated by TBHP/KI

图式35. 元素硫介导的三组分氧化还原反应

Scheme 35. Elemental sulfur mediated three component redox reaction

图式36. 苯并噻唑的C—H键官能化反应

Scheme 36. C—H bond functionalization of benzothiazoles

图式37. FeCl3催化N-杂芳基和芳基金属试剂的氧化偶联反应

Scheme 37. FeCl3 catalyzed oxidative coupling of N-heteroaryl and aryl metal reagents

图式38. 苯并噻唑芳基化合成2-苯基苯并噻唑

Scheme 38. Synthesis of 2-phenylbenzothiazole by arylation of benzothiazole

图式39. C—H键官能化反应合成2-取代苯并噻唑

Scheme 39. Synthesis of 2-substituted benzothiazoles by C—H bond functionalization

图式40. Pd/Cu催化苯并噻唑的酰基化反应

Scheme 40. Acylation of benzothiazole catalyzed by Pd/Cu

图式41. 硫代酰胺分子内环化的机理

Scheme 41. Mechanism of intramolecular cyclization of thioamides

图式42. 硫代酰胺衍生物分子内的环化反应

Scheme 42. Intramolecular cyclization of thioamide derivatives

图式43. 电化学介导的环化反应合成2-取代苯并噻唑

Scheme 43. Synthesis of 2-substituted benzothiazole by electrochemically mediated cyclization reaction

图式44. CuI催化合成2-取代苯并噻唑

Scheme 44. Synthesis of 2-substituted benzothiazoles catalyzed by CuI

图式45. N-苯基硫代酰胺的分子内环化

Scheme 45. Intramolecular cyclization of N-phenylthioamides

图式46. 分子间的偶联反应合成2-取代苯并噻唑

Scheme 46. Synthesis of 2-substituted benzothiazoles by intermolecular coupling reaction

图式47. 异腈化合物的分子内/分子间环化反应

Scheme 47. Intramolecular/intermolecular cyclization of isocyanide compounds

图式48. 2-氨基苯并噻唑的N-烷基化反应

Scheme 48. N-alkylation of 2-aminobenzothiazoles

图式49. Pd/Cu催化噻唑烷-2-硫酮与硼酸的偶联反应

Scheme 49. Coupling of thiazolidine-2-thiones and boric acids catalyzed by Palladium/copper

图式50. 过渡金属催化2-芳基苯并噻唑的合成

Scheme 50. Synthesis of 2-arylbenzothiazole catalyzed by transition metals

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