Progress in the Synthesis of Benzothiazole-2-ones

doi:10.6023/cjoc202504026

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (12): 4298-4314.DOI: 10.6023/cjoc202504026 Previous Articles Next Articles

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苯并噻唑-2-酮类化合物的合成研究进展

邢德悦^†, 王阳^†, 房亭轩, 解瑞俊, 李潇, 贾慧劼^*(), 竺宁^*()

内蒙古工业大学化工学院二氧化碳资源化利用自治区高等学校重点实验室内蒙古自治区CO₂捕集与资源化工程技术研究中心内蒙古自治区绿色化工重点实验室呼和浩特 010051

收稿日期:2025-04-14 修回日期:2025-07-11 发布日期:2025-08-26
通讯作者: 贾慧劼, 竺宁
作者简介:
^† 共同第一作者
基金资助:
国家自然科学基金(22379075); 内蒙古自治区直属高校基本科研业务费(JY20240076); 与内蒙古自治区党委人才工作领导小组“英才兴蒙”工程团队(2025TEL04)

Progress in the Synthesis of Benzothiazole-2-ones

Deyue Xing, Yang Wang, Tingxuan Fang, Ruijun Xie, Xiao Li, Huijie Jia^*(), Ning Zhu^*()

Key Laboratory of CO₂ Resource Utilization at Universities of Inner Mongolia Autonomous Region, Inner Mongolia Engineering Research Center for CO₂ Capture and Utilization, Inner Mongolia Key Laboratory of Green Chemical Engineering, Chemical Engineering College, Inner Mongolia University of Technology, Hohhot 010051

Received:2025-04-14 Revised:2025-07-11 Published:2025-08-26
Contact: Huijie Jia, Ning Zhu
About author:
^† These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(22379075); Basic Scientific Research Funds of Universities Directly under the Inner Mongolia Autonomous Region(JY20240076); Group Project of Developing Inner Mongolia through Talents from the Talents Work Leading Group under the CPC Inner Mongolia Autonomous Regional Committee(2025TEL04)

Benzothiazole-2-one, a fused cyclic compound incorporating a benzene ring with sulfur- and nitrogen-containing heterocycles, exhibits a broad spectrum of biological activities and holds significant application value in both agricultural and medicinal fields. Consequently, the synthesis methods of this compound have garnered considerable attention. This review identifies 2-aminobenzenethiol, 2-substituted benzothiazole, and o-haloaniline as the primary raw materials for synthesizing benzothiazole-2-one. Moreover, the methods, synthetic routes, and reaction mechanisms of using these three raw materials to synthesize benzothiazole-2-one have been systematically summarized, which offers valuable insights for the synthesis of these compounds. Additionally, the review also discusses the structural characteristics, reactivity, and atom economy of carbon- ylation reagents, providing a theoretical foundation for their application in organic synthesis.

Key words: benzothiazole-2-ones, synthesis method, reaction mechanism

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Deyue Xing, Yang Wang, Tingxuan Fang, Ruijun Xie, Xiao Li, Huijie Jia, Ning Zhu. Progress in the Synthesis of Benzothiazole-2-ones[J]. Chinese Journal of Organic Chemistry, 2025, 45(12): 4298-4314.

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Fig. & Tab. 44

Figure 1. Valuable application of benzothiazole-2-one derivatives

Scheme 1. Analysis of the method for the synthesis of benzothiazole-2-one

Scheme 2. Synthesis of benzothiazole-2-ones from the reaction of 2-aminothiophenol with carbonylation reagents

Scheme 3. Synthesis of benzothiazole-2-one from 2-aminothiophenol and CO catalyzed by S or Se

Scheme 4. Synthesis of benzothiazole-2-one from 2-aminothio- phenol and CO catalyzed by Pd

Scheme 5. Synthesis of benzothiazole-2-one from the reaction of 2-aminothiophenol and COY (Y=S/O)

Scheme 6. Synthesis of benzothiazol-2-one from the reaction of 2-aminothiophenol (or disulfide) and carbonyl sulfide

Scheme 7. Synthesis of benzothiazole-2-one from the reaction of 2-aminothiophenol and carbon dioxide catalyzed by ionic liquid or organic super base

Scheme 8. Synthesis of benzothiazole-2-one from the reaction of 2-aminothiophenol and supercritical carbon dioxide catalyzed by SnO

Scheme 9. Synthesis of benzothiazol-2-one from the reaction of 2-aminothiophenol and triphosgene

Scheme 10. Synthesis of benzothiazol-2-one from the reaction of 2-aminothiophenol and trifluoromethanesulfonic trifluoromethyl ester

Scheme 11. Synthesis of benzothiazole-2-one from the reaction of 2-aminothiophenol and ethyl chloroformate

Scheme 12. Synthesis of benzothiazole-2-one from the reaction of 2-aminothiophenol and methyl chloroformate

Scheme 13. Synthesis of benzothiazole-2-one from the reaction of 2-aminothiophenol and urea

Scheme 14. Synthesis of benzothiazole-2-one from the reaction of 2-aminothiophenol and N,N'-carbonyldiimidazole

Scheme 15. Formation of benzothiazole-2-one from the reaction of 2-aminothiophenol and 4,5-dichloropyridazine- 2-carboxylic acid phenyl ester

Scheme 16. Synthesis of benzothiazol-2-one from the reaction of 2-aminothiophenol and DSC

Scheme 17. Synthesis of benzothiazole-2-one from the reaction of 2-aminothiophenol and dithiocarbonate diester

Scheme 18. Synthesis of benzothiazol-2-one from the reaction of 2-aminothiophenol and phenyl isocyanate

Molecular weight	State of matter at room temperature	Carbonylation mechanism	Mass ratio of carbonyl groups in the reagent
27.99	Gas	CO undergoes in-situ conversion to COS/Se for participation in subsequent reactions or engages in direct reactions mediated by metal catalysis	100%
43.99	Gas	The carbonyl group is attacked by a nucleophile to form an amide or ester, which then participates in subsequent reactions	63.6%
59.97	Gas	The thiocarbonyl group is attacked by an amine nucleophile, forming thiocarbamate intermediates that subsequently engage in further reactions	46.7%
97.93	Gas	The acyl chloride is attacked by an amine nucleophile, forming carbamyl chloride that subsequently engage in further reactions	28.6%
293.80	Solid	Triphosgene cleaves into 3 equiv. of phosgene, which then participate in the reaction	28.6%
65.99	Gas	The acyl fluoride is attacked by an amine nucleophile, forming carbamyl fluoride that subsequently engage in further reactions	42.4%
217.95	Gas	The O—S bond cleavage yielded OCF₃ and F, generating acyl fluoride, which then participated in the reaction	12.8%
108.00	Liquid	The acyl chloride is attacked by an amine nucleophile, forming carbamate that subsequently engage in further reactions	25.9%
60.03	Solid	The urea is attacked by an amine nucleophile, forming another urea that subsequently engage in further reactions	46.6%
256.03	Solid	The electron-withdrawing inductive effect reduces the conjugation of the ester bond, facilitating the cleavage of the C—O bond to yield the carbonyl group	11.0%
382.04	Solid	The conjugation effect of the aromatic ring reduces the conjugation of the C—S bond in the thioester, promoting the cleavage of the C—S bond to form the carbonyl group	7.4%
162.05	Solid	The conjugation effect of the aromatic ring reduces the bond energy of the C—N bond in the amide, facilitating the cleavage of the C—N bond to yield the carbonyl group	17.2%
283.98	Liquid	The conjugation effect of the double bond facilitates the cleavage of the C—N bond in the amide, while the conjugation effect of the aromatic ring reduces the conjugation of the ester bond, promoting the cleavage of both the C—N and C—O bonds to yield the carbonyl group	9.8%
119.04	Liquid	The carbon atom in isocyanate, influenced by the electron-withdrawing inductive effects of both the oxygen and nitrogen atoms, is highly susceptible to nucleophilic attack, leading to the formation of urea or carbamate	23.5%

Molecular weight	State of matter at room temperature	Carbonylation mechanism	Mass ratio of carbonyl groups in the reagent
27.99	Gas	CO undergoes in-situ conversion to COS/Se for participation in subsequent reactions or engages in direct reactions mediated by metal catalysis	100%
43.99	Gas	The carbonyl group is attacked by a nucleophile to form an amide or ester, which then participates in subsequent reactions	63.6%
59.97	Gas	The thiocarbonyl group is attacked by an amine nucleophile, forming thiocarbamate intermediates that subsequently engage in further reactions	46.7%
97.93	Gas	The acyl chloride is attacked by an amine nucleophile, forming carbamyl chloride that subsequently engage in further reactions	28.6%
293.80	Solid	Triphosgene cleaves into 3 equiv. of phosgene, which then participate in the reaction	28.6%
65.99	Gas	The acyl fluoride is attacked by an amine nucleophile, forming carbamyl fluoride that subsequently engage in further reactions	42.4%
217.95	Gas	The O—S bond cleavage yielded OCF₃ and F, generating acyl fluoride, which then participated in the reaction	12.8%
108.00	Liquid	The acyl chloride is attacked by an amine nucleophile, forming carbamate that subsequently engage in further reactions	25.9%
60.03	Solid	The urea is attacked by an amine nucleophile, forming another urea that subsequently engage in further reactions	46.6%
256.03	Solid	The electron-withdrawing inductive effect reduces the conjugation of the ester bond, facilitating the cleavage of the C—O bond to yield the carbonyl group	11.0%
382.04	Solid	The conjugation effect of the aromatic ring reduces the conjugation of the C—S bond in the thioester, promoting the cleavage of the C—S bond to form the carbonyl group	7.4%
162.05	Solid	The conjugation effect of the aromatic ring reduces the bond energy of the C—N bond in the amide, facilitating the cleavage of the C—N bond to yield the carbonyl group	17.2%
283.98	Liquid	The conjugation effect of the double bond facilitates the cleavage of the C—N bond in the amide, while the conjugation effect of the aromatic ring reduces the conjugation of the ester bond, promoting the cleavage of both the C—N and C—O bonds to yield the carbonyl group	9.8%
119.04	Liquid	The carbon atom in isocyanate, influenced by the electron-withdrawing inductive effects of both the oxygen and nitrogen atoms, is highly susceptible to nucleophilic attack, leading to the formation of urea or carbamate	23.5%

Table 1. Carbonylation reagent for the preparation of benzothiazole-2-one using 2-aminothiophenol

Scheme 19. Reaction process for synthesizing benzothiazole- 2-one using 2-substituted benzothiazole as substrate

Scheme 20. Synthesis of benzothiazole-2-one from the hydrolysis of 2-chlorobenzothiazole

Scheme 21. Synthesis of benzothiazole-2-one from the hydrolysis of 2-chlorobenzothiazole mediated by hydrobromic acid

Scheme 22. Synthesis of benzothiazole-2-one from the reaction of 2-halogenated benzothiazole and hydroxylamine aqueous solution

Scheme 23. Synthesis of benzothiazole-2-one from the reaction of 2-fluorobenzothiazole and KOH

Scheme 24. Synthesis of benzothiazole-2-one from the diazotization and hydrolysis of 2-aminobenzothiazole derivatives

Scheme 25. Synthesis of benzothiazole-2-one from 2-amino- benzothiazole derivatives

Scheme 26. Synthesis of benzothiazol-2-one from the reaction of 2-mercaptobenzothiazole and methyl iodide

Scheme 27. Synthesis of benzothiazole-2-one from the reaction of 2-mercaptobenzothiazole and sodium hypochlorite

Scheme 28. Synthesis of benzothiazole-2-one from the oxidation reaction of 2H-benzothiazole

Scheme 29. Synthesis of benzothiazole-2-one from the reaction of benzothiazole and TBHP catalyzed by Cu

Scheme 30. Synthesis of benzothiazole-2-one from the decomposition of 2-substituted benzothiazole derivatives

Scheme 31. Synthesis of benzothiazole-2-one from the reaction of 2-(2-sulfonylbenzothiazole)-1-phenylethanone with 2,3-dimethyl- 1,3-butadiene

Scheme 32. Synthesis of benzothiazole-2-one from the decomposition of 2-benzothiazolyl-2-hydroxyphenethyl sulfide

Scheme 33. Reaction process for synthesizing benzothiazole- 2-one from ortho halogenated aniline

Scheme 34. Synthesis of benzothiazole-2-one from the reaction of 2-iodophenyl carbamate ethyl ester and Na2S

Scheme 35. Synthesis of benzothiazol-2-one from the reaction of o-iodoaniline, DMF and K2S

Scheme 36. Synthesis of benzothiazol-2-one from the reaction of o-haloaniline and potassium ethyl xanthate

Scheme 37. Synthesis of benzothiazol-2-one from the reaction of (2-bromophenyl)urea and mercaptopropionate

Scheme 38. Synthesis of benzothiazol-2-one from the reaction of o-bromophenyl isothiocyanate catalyzed by Cu

Scheme 39. Synthesis of benzothiazol-2-one from the reaction of aniline and CO2 catalyzed by tert-butoxide

Scheme 40. Synthesis of benzothiazol-2-one from the reaction of N,N-disubstituted arylhydrazine and CS2

Scheme 41. Synthesis of benzothiazol-2-one from the reaction of N-aryl thiocarbamoyl fluoride and water

Scheme 42. Synthesis of benzothiazol-2-one from the reaction of o-mercaptobenzoic acid and NH4N3

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苯并噻唑-2-酮类化合物的合成研究进展

Progress in the Synthesis of Benzothiazole-2-ones

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