Progress in Synthesis of 2-Substituted Benzothiazole Compounds

doi:10.6023/cjoc202007036

Abstract

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

Cite this article

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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Fig. & Tab. 50

Scheme 1. Reaction mechanism of 2-aminothiophenol with aldehydes

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

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

Scheme 4. Orthoboric acids mediated click cyclization

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

Scheme 6. Condensation of 2-aminothiophenols with aldehydes

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

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

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

Scheme 10. Electrochemically mediated decarboxylation coupling reaction

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

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

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

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

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

Scheme 16. Oxidative cyclization of 2-aminothiophenols with arylbenzylamines

Scheme 17. Reaction mechanism of 2-aminothiophenol with benzylamine

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

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

Scheme 20. Condensation of 2-aminothiophenols and alcohols

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

Scheme 22. Dehydrogenation of 2,3-dihydrobenzothiazoles

Scheme 23. Synthesis of 2-substituted benzothiazoles by dehydroaomatization

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

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

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

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

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

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

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

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

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

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

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

Scheme 35. Elemental sulfur mediated three component redox reaction

Scheme 36. C—H bond functionalization of benzothiazoles

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

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

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

Scheme 40. Acylation of benzothiazole catalyzed by Pd/Cu

Scheme 41. Mechanism of intramolecular cyclization of thioamides

Scheme 42. Intramolecular cyclization of thioamide derivatives

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

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

Scheme 45. Intramolecular cyclization of N-phenylthioamides

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

Scheme 47. Intramolecular/intermolecular cyclization of isocyanide compounds

Scheme 48. N-alkylation of 2-aminobenzothiazoles

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

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

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