2-氨基苯并噻唑类化合物的合成研究进展

doi:10.6023/cjoc202010002

有机化学 ›› 2021, Vol. 41 ›› Issue (4): 1498-1526.DOI: 10.6023/cjoc202010002 上一篇下一篇

综述与进展

2-氨基苯并噻唑类化合物的合成研究进展

侯秋飞^a, 张锐^a, 梁洁媚^a, 姚维忠^a, 程华^a^,^*(), 陈宬^b^,^*()

a 湖北文理学院食品化工学院湖北襄阳 441053
b 武汉理工大学材料复合新技术国家重点实验室武汉 430070

收稿日期:2020-10-02 修回日期:2020-10-27 发布日期:2020-11-04
通讯作者: 程华, 陈宬
基金资助:
国家自然科学基金(21502062); 湖北省教育厅指导基金(B2019135); 湖北文理学院教师科研能力培育基金(自然科学类); 湖北文理学院教师科研能力培育基金(2018kypy001); 湖北文理学院教师科研能力培育基金(2019kypy003); 湖北文理学院学科开放基金(XK2019038)

Progress in the Synthesis of 2-Aminobenzothiazoles

Qiufei Hou^a, Rui Zhang^a, Jiemei Liang^a, Weizhong Yao^a, Hua Cheng^a^,^*(), Cheng Chen^b^,^*()

a School of Food Science and Chemical Engineering, Hubei University of Arts and Science, Xiangyang, Hubei 441053
b State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070

Received:2020-10-02 Revised:2020-10-27 Published:2020-11-04
Contact: Hua Cheng, Cheng Chen
About author:
* Corresponding authors. E-mail: cch510@126.com;
E-mail: chengchen@whut.edu.cn.
Supported by:
National Natural Science Foundation of China(21502062); Scientific Research Program Guiding Project of Hubei Provincial Department of Education(B2019135); Teachers’ Scientific Research Ability Cultivation Fund of Hubei University of Arts and Science (Natural Science); Teachers’ Scientific Research Ability Cultivation Fund of Hubei University of Arts and Science(2018kypy001); Teachers’ Scientific Research Ability Cultivation Fund of Hubei University of Arts and Science(2019kypy003); Open Foundation of Discipline of Hubei University of Arts and Science(XK2019038)

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摘要/Abstract

2-氨基苯并噻唑类化合物是一类极其重要的氮杂环化合物, 在医药、农药等领域具有广阔的应用前景. 鉴于这类化合物多样的生物活性, 科研工作者们广泛关注并开发出很多新颖的合成方法. 系统总结了2-氨基苯并噻唑类化合物的合成方法, 按照合成原料的不同对这些方法进行了归类和分析, 并对其未来发展进行了展望.

关键词: N-取代, 2-氨基苯并噻唑, 胺化, C—H官能化, C—X活化, C—N交叉偶联, 成环, 合成

2-Aminobenzothiazoles are an important class of N-heterocyclic compounds which have been widely available in numerous bioactive compounds such as pharmaceuticals and agrochemicals. Due to the versatile biological activities, great attention has been paid to their synthesis. Therefore, multitudinous synthetic approaches have been developed for accessing these compounds, including the intramolecular cyclization of arylthioureas via C—H functionalization/C—S bond formation, the intramolecular cyclization of 2-haloarylthioureas via dehydrogenative C—S bond formation, and the intermolecular C—N cross-coupling of benzothiazole with amines, 2-chlorobenzothiazole with amines, 2-aminobenzothiazole with aryl halides,etc. In this paper, the syntheses of N-substituted 2-aminobenzothiazoles are systematically reviewed, and their synthetic methods are also classified and summarized based on the varieties of the utilized substrates. Finally, the future perspective of these compounds is described.

Key words: N-substituted, 2-aminobenzothiazole, amination, C—H functionalization, C—X activation, C—N cross-coupling, cyclization, synthesis

引用此文

侯秋飞, 张锐, 梁洁媚, 姚维忠, 程华, 陈宬. 2-氨基苯并噻唑类化合物的合成研究进展[J]. 有机化学, 2021, 41(4): 1498-1526.

Qiufei Hou, Rui Zhang, Jiemei Liang, Weizhong Yao, Hua Cheng, Cheng Chen. Progress in the Synthesis of 2-Aminobenzothiazoles[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1498-1526.

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图/表 53

图1. 含2-氨基苯并噻唑单元的生物活性分子

Figure 1. Bioactive molecules containing the 2-aminobenzothiazole unit

图式1. N-无取代2-氨基苯并噻唑的合成

Scheme 1. Synthesis of N-unsubstituted 2-aminobenzothiazole

图式2. 固相合成2-氨基苯并噻唑

Scheme 2. Solid phase synthesis of 2-aminobenzothiazoles

图式3. 电化学分子内C—H胺化合成2-氨基苯并噻唑

Scheme 3. Synthesis of 2-aminobenzothiazoles via electrochemical intramolecular C—H amination

图式4. 邻卤芳基硫脲分子内环化合成2-氨基苯并噻唑

Scheme 4. Synthesis of 2-aminobenzothiazoles from intramolecular cyclization of 2-haloarylthioureas

图式5. 无过渡金属条件下合成2-取代的苯并噻唑

Scheme 5. Transition-metal-free synthesis of 2-substituted benzothiazoles

图式6. R116010的工业化生产工艺

Scheme 6. Commercial process of R116010

图式7. 利用苄基三甲基三溴化铵合成2-氨基苯并噻唑

Scheme 7. Synthesis of 2-aminobenzothiazoles using benzyltrimethylammonium tribromide

图式8. 钯催化分子内氧化C—H官能化合成2-氨基苯并噻唑

Scheme 8. Synthesis of 2-aminobenzothiazoles from palladium-catalyzed intramolecular oxidative C—H functionalization

图式9. 钯催化C—H官能化合成2-氨基苯并噻唑

Scheme 9. Synthesis of 2-aminobenzothiazoles from palladium-catalyzed C—H functionalization

图式10. 芳基硫脲分子内环化合成2-氨基苯并噻唑

Scheme 10. Synthesis of 2-aminobenzothiazoles from the intramolecular cyclization of arylthioureas

图式11. 钌催化分子内C—S偶联合成2-氨基苯并噻唑

Scheme 11. Synthesis of 2-aminobenzothiazoles from ruthenium-catalyzed intramolecular C—S coupling

图式12. 钯催化分子内环化合成2-氨基苯并噻唑

Scheme 12. Synthesis of 2-aminobenzothiazoles by palladium- catalyzed intramolecular cyclization

图式13. 由邻碘苯基异硫氰酸酯与胺反应合成2-氨基苯并噻唑

Scheme 13. Synthesis of 2-aminobenzothiazoles from 2-iodo- phenylisothiocyanates and amines

图式14. 铜或钯催化合成2-氨基苯并噻唑

Scheme 14. Synthesis of 2-aminobenzothiazoles by Cu- or Pd- catalyzed reaction

图式15. 由2-卤苯基异硫氰酸酯与胺反应合成2-氨基苯并噻唑

Scheme 15. Synthesis of 2-aminobenzothiazoles from 2-halo- phenylisothiocyanates and amines

图式16. 铜催化选择性转化硫脲为硫代氨基胍和2-氨基苯并噻唑

Scheme 16. Cu-catalyzed selective transformation of thioureas to thioamidoguanidines and 2-aminobenzothiazoles

图式17. 由邻碘芳基异硫氰酸酯与胺反应合成2-芳氨基苯并噻唑

Scheme 17. Synthesis of 2-(arylamino)benzothiazoles from 2- iodoarylisothiocyanates and amines

图式18. 由邻卤芳胺与异硫氰酸酯反应合成N-取代的2-氨基苯并噻唑

Scheme 18. Synthesis of N-substituted 2-aminobenzothiazoles from 2-haloarylamines and isothiocyanates

图式19. Merrifield树脂负载的邻菲啰啉Cu(I)催化合成2-氨基苯并噻唑

Scheme 19. Synthesis of 2-aminobenzothiazoles catalyzed by a Merrifield resin supported phenanthroline Cu(I) complex

图式20. MCM-41负载的Cu(II)配合物催化合成2-氨基苯并噻唑

Scheme 20. Synthesis of 2-aminobenzothiazoles catalyzed by a MCM-41 immobilized Cu(II) complex

图式21. 由邻卤芳胺与异硫氰酸酯反应合成N-取代的2-氨基苯并噻唑

Scheme 21. Synthesis of N-substituted 2-aminobenzothiazoles from 2-haloarylamines and isothiocyanates

图式22. 铜催化水相一锅合成2-氨基苯并噻唑

Scheme 22. One-pot synthesis of 2-aminobenzothiazoles in water by copper catalysis

图式23. 铜催化水相合成N-取代的苯并杂环

Scheme 23. Copper-catalyzed synthesis of N-substituted benzoheterocycles in water

图式24. IRMOF-3负载的Cu(I)复合物催化合成2-氨基苯并噻唑

Scheme 24. Cu(I) complex immobilized on IRMOF-3 catalyzed synthesis of 2-aminobenzothiazoles

图式25. 由邻碘芳胺与芳基异硫氰酸酯反应合成N-取代的2-氨基苯并噻唑

Scheme 25. Synthesis of N-substituted 2-aminobenzothiazoles from 2-iodoarylamines and arylisothiocyanates

图式26. 二氧化硅包覆的磁性纳米粒子负载Cu(II)催化合成2-氨基苯并噻唑和吲哚

Scheme 26. Synthesis of 2-aminobenzothiazoles and indoles catalyzed by Cu(II) immobilized on silica-coated magnetite nanoparticles

图式27. 铜催化与钯催化合成2-氨基苯并噻唑

Scheme 27. Cu(II)-catalyzed and Pd(II)-catalyzed synthesis of 2-aminobenzothiazoles

图式28. 由芳基异硫氰酸酯与甲酰胺合成2-取代苯并噻唑

Scheme 28. Synthesis of 2-aminobenzothiazoles from arylisothiocyanates and formamides

图式29. 由两分子异硫氰酸酯反应合成N-苯基取代的2-氨基苯并噻唑

Scheme 29. Synthesis of 2-phenylaminobenzothiszoles from two isothiocyanates

图式30. 由邻氨基苯硫酚与异硫氰酸酯反应合成N-取代的2-氨基苯并噻唑

Scheme 30. Synthesis of N-substituted 2-aminobenzothiazoles from 2-aminothiophenols and isothiocyanates

图式31. 由邻氨基苯硫酚与异硫氰酸酯反应合成2-氨基苯并噻唑

Scheme 31. Synthesis of 2-aminobenzothiazoles from 2-amino- thiophenol and isothiocyanates

图式32. 由2,2'-二氨基二苯二硫醚与异硫氰酸酯反应合成2-氨基苯并噻唑

Scheme 32. Synthesis of 2-aminobenzothiazoles from 2,2'-dia- minodiphenyl disulfide and isothiocyanates

图式33. 由邻氨基苯硫酚与异腈反应合成2-氨基苯并噻唑

Scheme 33. Synthesis of 2-aminobenzothiazoles from 2-amino- thiophenols and isocyanides

图式34. 铜催化三组分合成N-取代的2-氨基苯并噻唑

Scheme 34. Copper-catalyzed three-component synthesis of 2-N-substituted benzothiszoles

图式35. 球磨条件下一锅合成2-氨基苯并噻唑

Scheme 35. One-pot synthesis of 2-aminobenzothiazoles under ball-milling

图式36. 金属催化的苯并噻唑C—H胺化反应

Scheme 36. Metal-catalyzed C—H amination of benzothiazoles

图式37. 铜催化氧化唑类化合物C—H、N—H偶联

Scheme 37. Copper-catalyzed oxidative C—H, N—H coupling of azoles

图式38. 2-氯苯并噻唑胺化合成2-氨基苯并噻唑

Scheme 38. Synthesis of 2-aminobenzothiazoles from the amination of 2-chlorobenzothiazoles

图式39. 钯催化卤代芳杂环胺化

Scheme 39. Pd-catalyzed amination of heteroaryl halides

图式40. 2-氯苯并噻唑胺化合成2-氨基苯并噻唑

Scheme 40. Synthesis of 2-aminobenzothiazoles from the amination of 2-chlorobenzothiazole

图式41. 钯催化与铜催化的2-卤苯并噻唑胺化反应

Scheme 41. Palladium-catalyzed versus copper-catalyzed amination of 2-halobenzothiazoles

图式42. 配体调控的钯催化选择性实现芳香伯胺的单/双芳基化

Scheme 42. Ligand-controlled palladium catalysis for selective mono- or di-arylation of primary aromatic amines

图式43. 钯催化杂环芳胺N-芳基化

Scheme 43. Pd-catalyzed N-arylation of heteroarylamines

图式44. 2-氨基苯并噻唑与卤代芳烃反应合成N-取代的2-氨基苯并噻唑

Scheme 44. Synthesis of N-substituted 2-aminobenzothiazoles from 2-aminobenzothiazole and aryl halides

图式45. 钯催化2-氨基苯并噻唑--芳基化

Scheme 45. Pd-catalyzed N-arylation of 2-aminobenzothiazoles

图式46. 2-氨基苯并噻唑与卤代芳烃反应合成N-取代的2-氨基苯并噻唑

Scheme 46. Synthesis of N-substituted 2-aminobenzothiazoles from 2-aminobenzothiazole and aryl halides

图式47. 2-氨基苯并噻唑衍生物与卤代芳烃反应合成N-取代的2-氨基苯并噻唑

Scheme 47. Synthesis of N-substituted 2-aminobenzothiazoles from 2-aminobenzothiazole and aryl halides

图式48. 利用吡喃盐对杂环芳胺进行C-N活化和功能化

Scheme 48. C—N activation and functionalization of aminoheterocycles by a pyrylium salt

图式49. 由芳基异硫脲与碘代芳烃反应合成N-芳基取代的2-氨基苯并噻唑

Scheme 49. Synthesis of 2-arylaminobenzothiszoles from arylisothioureas and aryl iodides

图式50. 铜促进的三组分合成2-氨基苯并噻唑衍生物

Scheme 50. Copper-mediated three-component approach to 2-aminobenzothiazole derivatives

图式51. 苯并三唑分子内裂解环化合成2-N-取代的苯并噻唑

Scheme 51. Synthesis of 2?N?substituted benzothiazoles via intramolecular cyclative cleavage of benzotriazole ring

图式52. 由环己酮和硫脲合成2-氨基苯并噻唑

Scheme 52. Synthesis of 2-aminobenzothiazoles from cyclohexanones and thioureas

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2-氨基苯并噻唑类化合物的合成研究进展

Progress in the Synthesis of 2-Aminobenzothiazoles

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