苯并噻唑-2-酮类化合物的合成研究进展

doi:10.6023/cjoc202504026

有机化学 ›› 2025, Vol. 45 ›› Issue (12): 4298-4314.DOI: 10.6023/cjoc202504026 上一篇下一篇

综述与进展

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)

文章分享

摘要/Abstract

苯并噻唑-2-酮是一种含有苯环和硫氮杂环的稠环化合物, 具有广泛的生物活性, 在农业及医药领域有着较高的应用价值, 其合成方法的研究也备受关注. 本综述通过调研文献发现2-氨基苯硫酚、2-取代苯并噻唑以及邻卤苯胺是合成苯并噻唑-2-酮的主要原料, 并系统总结了这三种原料合成苯并噻唑-2-酮的方法、路线及其反应机理, 为该类化合物的合成提供了参考依据. 此外, 本综述还探讨了羰基化试剂的结构特点、反应活性以及原子经济性, 为羰基化试剂在有机合成中的应用提供了理论依据.

关键词: 苯并噻唑-2-酮, 合成方法, 反应机理

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

引用此文

邢德悦, 王阳, 房亭轩, 解瑞俊, 李潇, 贾慧劼, 竺宁. 苯并噻唑-2-酮类化合物的合成研究进展[J]. 有机化学, 2025, 45(12): 4298-4314.

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 44

图1. 苯并噻唑-2-酮类衍生物的应用价值

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

图式1. 苯并噻唑-2-酮的合成方法分析

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

图式2. 2-氨基苯硫酚与羰基化试剂反应合成苯并噻唑-2-酮

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

图式3. S或Se催化CO与2-氨基苯硫酚反应合成苯并噻唑-2-酮

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

图式4. Pd催化CO与2-氨基苯硫酚合成苯并噻唑-2-酮

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

图式5. 2-氨基苯硫酚和COY (Y=S/O)反应生成苯并噻唑-2-酮

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

图式6. 2-氨基苯硫酚(或其二硫化物)与羰基硫反应合成苯并噻唑-2-酮

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

图式7. 2-氨基苯硫酚与二氧化碳在离子液体或有机超碱催化下反应合成苯并噻唑-2-酮

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

图式8. 2-氨基苯硫酚与超临界二氧化碳在SnO催化下反应合成苯并噻唑-2-酮

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

图式9. 2-氨基苯硫酚与三光气反应合成苯并噻唑-2-酮

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

图式10. 2-氨基苯硫酚与三氟甲烷磺酸三氟甲酯反应合成苯并噻唑-2-酮

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

图式11. 2-氨基苯硫酚与氯甲酸乙酯反应合成苯并噻唑-2-酮

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

图式12. 2-氨基苯硫酚与氯甲酸甲酯反应合成苯并噻唑-2-酮

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

图式13. 2-氨基苯硫酚与尿素反应合成苯并噻唑-2-酮

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

图式14. 2-氨基苯硫酚与N,N'-羰基二咪唑反应合成苯并噻唑-2-酮

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

图式15. 2-氨基苯硫酚与4,5-二氯哒嗪-2-羧酸苯酯反应生成苯并噻唑-2-酮

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

图式16. 2-氨基苯硫酚与DSC反应合成苯并噻唑-2-酮

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

图式17. 2-氨基苯硫酚与二硫代碳酸二酯反应合成苯并噻唑-2-酮

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

图式18. 2-氨基苯硫酚与异氰酸苯酯反应合成苯并噻唑-2-酮

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%

表1. 多种羰基化试剂的特点及其性质

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

表1. 多种羰基化试剂的特点及其性质

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

图式19. 以2-取代苯并噻唑为底物合成苯并噻唑-2-酮的反应过程

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

图式20. 2-氯苯并噻唑水解合成苯并噻唑-2-酮

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

图式21. 2-氯苯并噻唑在氢溴酸的作用下水解合成苯并噻唑-2-酮

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

图式22. 2-卤代苯并噻唑与羟胺水溶液反应合成苯并噻唑-2-酮

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

图式23. 2-氟苯并噻唑与KOH反应合成苯并噻唑-2-酮

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

图式24. 2-氨基苯并噻唑类衍生物重氮化水解合成苯并噻唑-2-酮

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

图式25. 2-氨基苯并噻唑衍生物合成苯并噻唑-2-酮

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

图式26. 2-巯基苯并噻唑与碘甲烷反应合成苯并噻唑-2-酮

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

图式27. 2-巯基苯并噻唑与次氯酸钠反应合成苯并噻唑-2-酮

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

图式28. 2H-苯并噻唑氧化合成苯并噻唑-2-酮

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

图式29. 苯并噻唑与TBHP在铜催化下反应合成苯并噻唑-2-酮

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

图式30. 2-取代苯并噻唑类衍生物分解为苯并噻唑-2-酮

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

图式31. 2-(2-亚砜基苯并噻唑)-1-苯乙酮与2,3-二甲基-1,3-丁二烯反应合成苯并噻唑-2-酮

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

图式32. 2-苯并噻唑基-2-羟基苯乙基硫醚分解为苯并噻唑-2-酮

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

图式33. 以邻卤苯胺为底物合成苯并噻唑-2-酮的反应过程

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

图式34. (2-碘苯基)氨基甲酸乙酯与Na2S合成苯并噻唑-2-酮

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

图式35. 邻碘苯胺、DMF与K2S反应合成苯并噻唑-2-酮

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

图式36. 邻卤苯胺与乙基黄原酸钾反应合成苯并噻唑-2-酮

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

图式37. 邻溴苯基脲与巯基丙酸酯反应合成苯并噻唑-2-酮

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

图式38. 邻溴苯基异硫氰酸酯在Cu催化下合成苯并噻唑-2-酮

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

图式39. 苯胺、CO2和S8在叔丁醇碱催化下反应合成苯并噻唑-2-酮

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

图式40. N,N-二取代芳基肼和CS2反应合成苯并噻唑-2-酮

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

图式41. N-芳基硫代氨基甲酰氟和水反应合成苯并噻唑-2-酮

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

图式42. 邻巯基苯甲酸和NH4N3反应合成苯并噻唑-2-酮

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

参考文献 68

[5]	Oida T. J. Biochem. 1986, 100, 99. pmid: 3759941
[6]	Alghamdi A. A.; Alam M. M.; Nazreen S. Turk. J. Chem. 2020, 44, 1068. doi: 10.3906/kim-1912-55 pmid: 33488213
[7]	Ucar H.; Van K.; Cacciaguerra S.; Spampinato S.; Stables J. P.; Depovere P.; Isa M.; Masereel B.; Delarge J.; Poupaert J. P. J. Med. Chem. 1998, 41, 1138. pmid: 9544213
[8]	Fairhurst R. A.; Janus D.; Lawrence A. Org. Lett. 2005, 7, 4697. pmid: 16209513
[9]	Hashihayata T.; Mandai H.; Mukaiyama T. Bull. Chem. Soc. Jpn. 2004, 77, 169. doi: 10.1246/bcsj.77.169
[10]	Ramachandran M.; Anandan S. New J. Chem. 2020, 44, 6186. doi: 10.1039/d0nj00273a
[11]	Besthorn E. Ber. Dtsch. Chem. Ges. 1910, 43, 1519. doi: 10.1002/cber.v43:2
[12]	Liu X.; Dong Z. B. Eur. J. Org. Chem. 2020, 2020, 408. doi: 10.1002/ejoc.v2020.4
[13]	Sonoda N.; Yamamoto G.; Natsukawa K.; Kondo K.; Murai S. Tetrahedron Lett. 1975, 16, 1969. doi: 10.1016/S0040-4039(00)72336-7
[14]	Mizuno T.; Toba H.; Miyata T.; Nishiguchi I. Heteroat. Chem. 1994, 5, 437. doi: 10.1002/hc.v5:5/6
[15]	Konishi K.; Nishiguchi I.; Hirashima T. Synthesis 1984, 254.
[16]	Shi G. H.; Du Y. Z.; Gao Y. Y.; Jia H. J.; Hong H. L.; Han L. M.; Zhu N. Chin. J. Org. Chem. 2023, 43, 491. (in Chinese)
	(时广辉, 杜云哲, 高媛媛, 贾慧劼, 洪海龙, 韩利民, 竺宁, 有机化学, 2023, 43, 491.) doi: 10.6023/cjoc202207029
[17]	Troisi L.; Granito C.; Perrone S.; Rosato F. Tetrahedron Lett. 2011, 52, 4330. doi: 10.1016/j.tetlet.2011.06.049
[18]	Cheng S. L.; Wu J. K.; Jia H. J.; Xie R. J.; Zhu N. J. Org. Chem. 2023, 88, 17297. doi: 10.1021/acs.joc.3c02140
[19]	Zhou B. H.; Hong H. L.; Wang H. C.; Zhang T. M.; Han L. M.; Zhu N. Eur. J. Org. Chem. 2018, 48, 6983.
[20]	D’Amico J. J.; Fuhrhop R. W.; Bollinger F. G.; Dahl W. E. J. Heterocycl. Chem. 1986, 23, 641. doi: 10.1002/jhet.v23:3
[21]	Yu B.; Zhang H. Y.; Zhao Y. F.; Chen S.; Xu J. L.; Hao L. D.; Liu Z. M. ACS Catal. 2013, 3, 2076. doi: 10.1021/cs400256j
[22]	Zhao Y. F.; Wu Y. Y.; Yuan G. F.; Hao L. D.; Gao X.; Yang Z. Z.; Yu B.; Zhang H. Y.; Liu Z. M. Chem. Asian J. 2016, 11, 2735. doi: 10.1002/asia.v11.19
[23]	Gao X.; Deng Y. H.; Lu C. Y.; Zhang L.; Wang X. T.; Yu B. Catalysts 2018, 8, 271. doi: 10.3390/catal8070271
[24]	Cao X. T.; Zhong H. Z. A.; Zhang P. F.; Zheng H. J. CO₂ Util. 2018, 24, 250.
[25]	Panov Y. M.; Erkhova L. V.; Balybin A. G. Krut'ko D. P.; Leme- novskii D. A. Russ. J. Phys. Chem. B 2019, 13, 1284. doi: 10.1134/S1990793119080062
[26]	Bard A. J. J. Am. Chem. Soc. 1930, 62, 125.
[27]	Jakobsson J. E.; Lu S. Y.; Telu S.; Pike V. W. Angew. Chem., Int. Ed. 2020, 59, 7256. doi: 10.1002/anie.201915414 pmid: 31995256
[28]	Song H. X.; Han Z. Z.; Zhang C. P. Chem.-Eur. J. 2019, 25, 10907. doi: 10.1002/chem.v25.46
[29]	Tasdelen M. A.; Yagci Y. Angew. Chem., Int. Ed. 2013, 52,5930. doi: 10.1002/anie.201208741 pmid: 23653429
[30]	Singh M. S.; Singh P.; Singh S. Indian J. Chem. 2007, 46, 1666.
[31]	Velikorodov A. V.; Kuanchalieva A. K.; Melent’eva E. A.; Titova O. L. Russ. J. Org. Chem. 2011, 47, 1375. doi: 10.1134/S107042801109020X
[32]	Fife T. H.; Hutchins J. E. C.; Wang M. S. J. Am. Chem. Soc. 1975, 97, 5878. doi: 10.1021/ja00853a038
[33]	Önkol T.; Dündar Y.; Yıldırım E.; Erol K.; Sahin M. F. Arzneimittelforschung 2012, 62, 571. doi: 10.1055/s-00000175
[34]	Bala M.; Verma P. K.; Sharma D.; Kumar N.; Singh B. Mol. Diversity 2015, 19, 263. doi: 10.1007/s11030-015-9572-8
[35]	Seminerio M. J.; Robson M. J.; Abdelazeem A. H.; Mesangeau C.; Jamalapuram S.; Avery B. A.; McCurdy C. R.; Matsumoto R. R. AAPS J. 2012, 14, 43. doi: 10.1208/s12248-011-9311-8 pmid: 22183188
[36]	Ryu K. E.; Kim B. R.; Sung G. H.; Yoon H. J.; Yoon Y. J. Synlett 2015, 26, 1985. doi: 10.1055/s-00000083
[37]	Takeda K.; Ogura H. Synth. Commun. 1982, 12, 213. doi: 10.1080/00397918208063680
[38]	Takeda K.; Tsuboyama K.; Takayanagi H.; Shirokami R.; Takeura M.; Ogura H. Chem. Pharm. Bull. 1989, 37, 2334. doi: 10.1248/cpb.37.2334
[39]	Lou C.Q.; Zhu N.; Fan R.H.; Hong H. L.; Han L. M.; Zhang J. B.; Suo Q. L. Green Chem. 2017, 19, 1102. doi: 10.1039/C6GC03053J
[40]	Jing Y. F.; Liu R. T.; Lin Y. H.; Zhou X. G. Sci. China Chem. 2014, 57, 1117. doi: 10.1007/s11426-014-5149-0
[41]	Qian X. H.; Li Z. G.; Yang Q. Bioorg. Med. Chem. 2007, 15, 6846. doi: 10.1016/j.bmc.2007.07.008
[42]	Foye W. O.; Abood N.; Kauffman J. M.; Kim Y. H.; Patel B. R. Phosphorus, Sulfur Silicon Relat. Elem. 1980, 8, 205.
[43]	Zhu L.; Zhang M. B.; Dai M. J. Heterocycl. Chem. 2005, 42, 727. doi: 10.1002/jhet.v42:4
[44]	Giles M. E.; Thomson C.; Eyley S. C.; Cole A. J.; Goodwin C. J.; Hurved P. A.; Morlin A. J. G.; Tornos J.; Atkinson S.; Just C.; Dean J. C.; Singleton J. T.; Longton A. J.; Woodland I.; Teasdale A.; Gregertsen B.; Else H.; Athwal M. S.; Tatterton S.; Knott J. M.; Thompson Nicola.; Smith S. J. Org. Process Res. Dev. 2004, 8, 628. doi: 10.1021/op049953y
[45]	Nociarova J.; Osusky P.; Rakovsky E.; Georgiou D.; Polyzos I.; Fakis M.; Hrobarik P. Org. Lett. 2021, 23, 3460. doi: 10.1021/acs.orglett.1c00893
[46]	Patil D. G.; Chedekel M. R. J. Org. Chem. 1984, 49, 997. doi: 10.1021/jo00180a009
[47]	Weinstock J.; Gaitanopoulos D. E.; Stringer O. D.; Franz R. G.; Hieble J. P.; Kinter L. B.; Mann W. A.; Flaim K. E.; Gessners G. J. Med. Chem. 1987, 30, 1166. pmid: 2955118
[48]	Kamps J. J. A. G.; Belle R.; Mecinović J. Org. Biomol. Chem. 2013, 11, 1103. doi: 10.1039/c2ob26929e pmid: 23224221
[49]	Rodrigo E.; Wiechert R.; Walter M. W.; Braje W.; Geneste H. Green Chem. 2022, 24, 1469. doi: 10.1039/D1GC04361G
[50]	D’Amico J. J.; Bollinger F. G. J. Heterocycl. Chem. 1988, 25, 1183. doi: 10.1002/jhet.v25:4
[51]	Liu Q.; Wu P.; Yang Y. H.; Zeng Z. Q.; Liu J.; Yi H.; Lei A. W. Angew. Chem., Int. Ed. 2012, 51, 4666. doi: 10.1002/anie.v51.19
[52]	Chen L.; Li X. Z.; Xu K. L.; Xu Q.; Liu Y.; Liu P. Eur. J. Org. Chem. 2024, 27, e202301108 doi: 10.1002/ejoc.v27.1
[53]	Tezuka N.; Shimojo K.; Hirano K.; Komagawa S.; Yoshida K.; Wang C.; Miyamoto K.; Saito T.; Takita R.; Uchiyama R. J. Am. Chem. Soc. 2016, 138, 9166. doi: 10.1021/jacs.6b03855
[54]	Yamada N.; Mizuochi M.; Morita H. Tetrahedron 2007, 63, 3408. doi: 10.1016/j.tet.2007.01.043
[55]	Shibata K.; Mitsunobu O. Bull. Chem. Soc. Jpn. 1992, 65, 3163. doi: 10.1246/bcsj.65.3163
[56]	Morita H.; Takeda M.; Kamiyama H.; Hashimoto T.; Youshimura T.; Shimasaki C.; Tsukurimichi E. Tetrahedron Lett. 1996, 37, 3739.
[57]	Aversa M. C.; Barattucci A.; Bonaccorsi P.; Giannetto P. Tetrahedron 2002, 58, 10145. doi: 10.1016/S0040-4020(02)01365-0
[58]	Li J. J.; Zhang Y. H.; Jiang Y. W.; Ma D. W. Tetrahedron Lett. 2012, 53, 2511. doi: 10.1016/j.tetlet.2012.03.006
[59]	Yang Y.; Zhang X. Y.; Zeng W. L.; Huang H.; Liang Y. RSC Adv. 2014, 4, 6090. doi: 10.1039/c3ra46803h
[60]	Tzanova T.; Gerova M.; Petrov O.; Karaivanova M.; Bagrel D. Eur. J. Med. Chem. 2009, 44, 2724. doi: 10.1016/j.ejmech.2008.09.010
[61]	Singh B.; Pennock P. O.; Lesher G. Y.; Bacon E. R.; Page D. F. Heterocycles 1993, 36, 133. doi: 10.3987/COM-92-6193
[62]	Itoh T.; Mase T. Org. Lett. 2007, 9, 3687. doi: 10.1021/ol7015737
[63]	Murru S.; Mondal P.; Yella R.; Patel B. K. Eur. J. Org. Chem. 2009, 5406.
[64]	Wei X. Y.; Wang X. M. Inorg. Chem. Commun. 2021, 128, 108590. doi: 10.1016/j.inoche.2021.108590
[65]	Ran C. K.; Song L.; Niu Y. N.; Wei M. K.; Zhang Z.; Zhou X. Y.; Yu D. G. Green Chem. 2021, 23, 274. doi: 10.1039/D0GC03723K
[66]	Zhuo X. Y.; Zheng L. Y.; Zou X. Y.; Zhong Y. M.; Guo W. J. Org. Chem. 2022, 87, 10467. doi: 10.1021/acs.joc.2c01060
[1]	Weng J. Q.; Liu X. H.; Huang H.; Tan C. X.; Chen J. Molecules 2012, 17, 989. doi: 10.3390/molecules17010989
[2]	Schroll R.; Becher H. H.; Dörfler U.; Gayler S.; Grundmann S.; Hartmann H. P.; Ruoss J. U. Environ. Sci. Technol. 2006, 40, 3305. doi: 10.1021/es052205j
[3]	Hiesinger K.; Schott A.; Kramer J. S. Blocher R.; Witt F.; Wittmann S. K.; Steinhilber D.; Pogoryelov D.; Gerstmeier J.; Werz O.; Proschak E. ACS Med. Chem. Lett. 2020, 11, 298. doi: 10.1021/acsmedchemlett.9b00330 pmid: 32184960
[4]	Abdelazeem A. H.; Khan S. I.; White S. W.; Sufka K. J.; McCurdy C. R. Bioorg. Med. Chem. 2015, 23, 3248.
[67]	Yu M.; Zhen L.; Jiang L. Q. Adv. Synth. Catal. 2022, 364, 1. doi: 10.1002/adsc.v364.1
[68]	Sridhar R.; Perumal P. T. Synth. Commun. 2004, 34,735. doi: 10.1081/SCC-120027722

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

RichHTML

PDF

可视化

摘要/Abstract

引用此文

分享此文

图/表 44

参考文献 68

相关文章 15

编辑推荐

相关统计

本文评价

[1]	刘小宇, 许庭瑞, 秦勇. 吗啡类生物碱的全合成研究新进展^★[J]. 有机化学, 2025, 45(9): 3098-3112.
[2]	林天星, 刘天飞. N-三氟甲基酰胺合成方法的研究进展[J]. 有机化学, 2025, 45(6): 1995-2006.
[3]	李闯, 张成, 刘小宇, 秦勇. 二萜生物碱全合成研究进展[J]. 有机化学, 2025, 45(3): 881-895.
[4]	何卫保, 易荣楠, 杨梓, 伍智林, 何卫民. Langlois试剂在电化学三氟甲基化反应中的应用进展[J]. 有机化学, 2025, 45(10): 3534-3545.
[5]	郭国菊, 吴启龙, 董宇振, 张洁, 石永佳, 柳清, 杨道山. 光/电化学驱动硫代磷酸酯类化合物的合成研究进展[J]. 有机化学, 2025, 45(10): 3719-3740.
[6]	刘艺琦, 陈文婕, 赵泽艳, 王苏棋, 唐圣松, 何卫民, 彭俊梅. 关于8种含氮杂环光催化合成的研究进展[J]. 有机化学, 2025, 45(10): 3546-3586.
[7]	周岑, 赵新, 张霄. 三聚苯环化反应的研究进展[J]. 有机化学, 2025, 45(1): 42-55.
[8]	曹素芳, 刘云云, 万结平. α-三氟甲基酮的合成及其脱氟转化反应研究进展[J]. 有机化学, 2025, 45(1): 86-103.
[9]	张雅芳, 黄轩, 林琪, 钟海琼, 翁志强, 吴伟. 噻唑类化合物的合成研究进展[J]. 有机化学, 2024, 44(5): 1458-1479.
[10]	关丽, 周艳艳, 毛永爆, 付恺森, 关文惠, 付义乐. 甲川链修饰菁染料的合成研究进展[J]. 有机化学, 2023, 43(8): 2682-2698.
[11]	宋树勇, 徐森苗. 三氟甲基烯烃的选择性C-F键活化最新进展[J]. 有机化学, 2023, 43(2): 411-425.
[12]	刘悦灵, 钟欣欣, 张干兵. Pd(0)催化1-R-3-苯基亚丙基环丙烷(R=Me/H)与呋喃甲醛[3＋2]环加成反应机理的密度泛函理论研究[J]. 有机化学, 2023, 43(2): 660-667.
[13]	刘婷婷, 胡宇才, 沈安. 亚胺配体协同氮杂环卡宾钯配合物催化碳碳偶联反应的作用机制[J]. 有机化学, 2023, 43(2): 622-628.
[14]	刘鹏, 钟富明, 廖礼豪, 谭伟强, 赵晓丹. 炔烃参与的去芳构化反应构建螺环己二烯酮类化合物的研究进展[J]. 有机化学, 2023, 43(12): 4019-4035.
[15]	黄泽鑫, 尹宇强, 贾丰成, 吴安心. 吲哚及其衍生物C2—C3键断裂的反应研究进展[J]. 有机化学, 2022, 42(7): 2028-2044.