Progress in the Synthesis of 2-Aminobenzothiazoles

doi:10.6023/cjoc202010002

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1498-1526.DOI: 10.6023/cjoc202010002 Previous Articles Next Articles

REVIEWS

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)

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

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 53

Figure 1. Bioactive molecules containing the 2-aminobenzothiazole unit

Scheme 1. Synthesis of N-unsubstituted 2-aminobenzothiazole

Scheme 2. Solid phase synthesis of 2-aminobenzothiazoles

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

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

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

Scheme 6. Commercial process of R116010

Scheme 7. Synthesis of 2-aminobenzothiazoles using benzyltrimethylammonium tribromide

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 29. Synthesis of 2-phenylaminobenzothiszoles from two isothiocyanates

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

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

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

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

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

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

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

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

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

Scheme 39. Pd-catalyzed amination of heteroaryl halides

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

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

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

Scheme 43. Pd-catalyzed N-arylation of heteroarylamines

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

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

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

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

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

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

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

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

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

References 168

[1]	Gill, R.K.; Rawal, R.K.; Bariwal, J. Arch. Pharm. Chem. Life Sci. 2015, 348,155.
[2]	Facchinetti, V.; Reis, R.R.; Gomes, C.R. B.; Vasconcelos, T.R. A. Mini-Rev. Org. Chem. 2012, 9,44.
[3]	Pathak, N.; Rathi, E.; Kumar, N.; Kini, S.G.; Rao, C.M. Mini-Rev. Med. Chem. 2020, 20,12. pmid: 31288719
[4]	Irfan, A.; Batool, F.; Naqvi, S.A. Z.; Islam, A.; Osman, S.M.; Nocentini, A.; Alissa, S.A.; Supuran, C.T. J. Enzyme Inhib. Med. Chem. 2020, 35,265.
[5]	Sharma, P.C.; Bansal, K.K.; Deep, A.; Pathak, M. Curr. Top. Med. Chem. 2017, 17,208.
[6]	Gagoria, J.; Verma, P.K.; Khatkar, A. Cent. Nerv. Syst. Agents Med. Chem. 2015, 15,11.
[7]	Jiang, K.; Cao, L.; Hao, Z.-F.; Chen, M.Y.; Cheng, J.-L.; Li, X.; Xiao, P.; Chen, L.; Wang, Z.-Y. Chin. J. Org. Chem. 2017, 37,2221. (in Chinese)
	( 蒋凯, 曹梁, 郝志峰, 陈美燕, 程洁銮, 李晓, 肖萍, 陈亮, 汪朝阳, 有机化学, 2017, 37,2221.)
[8]	Ballari, M.S.; Cano, N.H.; Lopez, A.G.; Wunderlin, D.A.; Feresin, G.; Santiago, A.N. J. Agric. Food Chem. 2017, 65,10325.
[9]	Si, W.-J.; Chen, M.; Wang, X.-L.; Wang, M.-Q.; Jiao, J.; Fu, X.-C.; Yang, C.-L. ARKIVOC 2018, 7,86.
[10]	Tariq, S.; Kamboj, P.; Amir, M. Arch. Pharm. Chem. Life Sci. 2018, 352,e1800170.
[11]	Kamal, A.; Syed, M.A. H.; Mohammed, S.M. Expert Opin. Ther. Pat. 2015, 25,355.
[12]	Keri, R.S.; Patil, M.R.; Patil, S.A.; Budagumpi, S. Eur. J. Med. Chem. 2015, 89,207. pmid: 25462241
[13]	Hu, Y.-X.; Xia, X.; He, W.-Z.; Tang, Z.-J.; Lv, Y.-L.; Li, X.; Zhang, D.-Y. Org. Electron. 2019, 66,126.
[14]	Zhang, M.; Liang, G. Sci. China: Chem. 2018, 61,1088.
[15]	Maruszewska, A.; Podsiadly, R. Color. Technol. 2014, 130,243.
[16]	Ghosh, P.; Katare, S.; Patkar, P.; Caruthers, J.M.; Venkatasubramanian, V.; Walker, K.A. Rubber Chem. Technol. 2003, 76,592.
[17]	Orlita, A. Int. Biodeterior. Biodegrad. 2004, 53,157.
[18]	Liao, C.; Kim, U.-J.; Kannan, K. Environ. Sci. Technol. 2018, 52,5007.
[19]	Li, Y.; Wang, Y.-L. Chin. J. Org. Chem. 2006, 26,878. (in Chinese)
	( 李焱, 王玉炉, 有机化学, 2006, 26,878.)
[20]	Noel, S.; Cadet, S.; Gras, E.; Hureau, C. Chem. Soc. Rev. 2013, 42,7747.
[21]	Zhu, N.; Zhang, Z.-W.; Gao, M.; Han, L.-M.; Suo, Q.-L.; Hong, H.-L. Chin. J. Org. Chem. 2013, 33,1423. (in Chinese)
	( 竺宁, 张志伟, 高敏, 韩利民, 索全伶, 洪海龙, 有机化学, 2013, 33,1423.)
[22]	Prajapati, N.P.; Vekariya, R.H.; Borad, M.A.; Patel, H.D. RSC Adv. 2014, 4,60176.
[23]	Dai, X.-Q.; Zhu, Y.-B.; Wang, Z.-Y.; Weng, J.-Q. Chin. J. Org. Chem. 2017, 37,1924. (in Chinese)
	( 戴小强, 朱亚波, 汪洲洋, 翁建全, 有机化学, 2017, 37,1924.)
[24]	Liu, X.; Dong, Z.-B. Eur. J. Org. Chem. 2020, 2020,408.
[25]	Gan, F.; Luo, P.; Lin, J.; Ding, Q. Synthesis 2020,DOI: 10.1055/s-0040-1707208.
[26]	Sweeney, J.B.; Rattray, M.; Pugh, V.; Powell, L.A. ACS Med. Chem. Lett. 2018, 9,552.
[27]	Navarro, S.; Bermejo, S.; Vela, N.; Hernández, J. J. Agric. Food Chem. 2009, 57,6375.
[28]	Verfaille, C.J.; Borgers, M.; Steensel, M.A. M. J. Dtsch. Dermatol. Ges. 2008, 6,355.
[29]	Baert, B.; Spiegeleer, B.D. Skin Pharmacol. Physiol. 2011, 24,151.
[30]	Xie, Y.; Deng, S.; Chen, Z.; Yan, S.; Landry, D.W. Bioorg. Med. Chem. Lett. 2006, 16,4657.
[31]	Hroch, L.; Guest, P.; Benek, O.; Soukup, O.; Janockova, J.; Dolezal, R.; Kuca, K.; Aitken, L.; Smith, T.K.; Gunn-Moore, F.; Zala, D.; Ramsay, R.R.; Musilek, K. Bioorg. Med. Chem. 2017, 25,1143.
[32]	Koppireddi, S.; Komsani, J.R.; Avula, S.; Pombala, S.; Vasamsetti, S.; Kotamraju, S.; Yadla, R. Eur. J. Med. Chem. 2013, 66,305.
[33]	Haroun, M.; Tratrat, C.; Kositsi, K.; Tsolaki, E.; Petrou, A.; Aldhubiab, B.; Attimarad, M.; Harsha, S.; Geronikaki, A.; Venugopala, K.N.; Elsewedy, H.S.; Sokovic, M.; Glamoclija, J.; Ciric, A. Curr. Top. Med. Chem. 2018, 18,75.
[34]	Thakkar, S.S.; Thakor, P.; Ray, A.; Doshi, H.; Thakkar, V.R. Bioorg. Med. Chem. 2017, 25,5396.
[35]	Xiao, H.; Li, P.; Hu, D.; Song, B.A. Bioorg. Med. Chem. Lett. 2014, 24,3452.
[36]	Siddiqui, N.; Alam, M.S.; Sahu, M.; Naim, M.J.; Yar, M.S.; Alam, O. Bioorg. Chem. 2017, 71,230.
[37]	Telvekar, V.N.; Bairwa, V.; Satardekar, K.; Bellubi, A. Bioorg. Med. Chem. Lett. 2012, 22,649. pmid: 22079026
[38]	Catalano, A.; Carocci, A.; Defrenza, I.; Muraglia, M.; Carrieri, A.; Bambeke, F.V.; Rosato, A.; Corbo, F.; Franchini, C. Eur. J. Med. Chem. 2013, 64,357.
[39]	Navarrete-Vazquez, G.; Ramírez-Martínez, M.; Estrada-Soto, S.; Nava-Zuazo, C.; Paoli, C.; Camici, G.; Escalante-García, J.; Medina-Franco, J.L.; Lόpez-Vallejo, F.; Ortiz-Andrade, R. Eur. J. Med. Chem. 2012, 53,346. pmid: 22583779
[40]	Venugopala, K.N.; Krishnappa, M.; Nayak, S.K.; Subrahmanya, B.K.; Vaderapura, J.P.; Chalannavar, R.K.; Gleiser, R.M.; Odhav, B. Eur. J. Med. Chem. 2013, 65,295.
[41]	Tariq, S.; Kamboj, P.; Alam, O.; Amir, M. Bioorg. Chem. 2018, 81,630.
[42]	Pitta, E.; Geronikaki, A.; Surmava, S.; Eleftheriou, P.; Mehta, V.P.; Van der Eycken, E.V. J. Enzyme Inhib. Med. Chem. 2013, 28,113.
[43]	Noolvi, M.N.; Patel, H.M.; Kaur, M. Eur. J. Med. Chem. 2012, 54,447.
[44]	Jordan, A.D.; Luo, C.; Reitz, A.B. J. Org. Chem. 2003, 68,8693. pmid: 14575503
[45]	Dadmal, T.L.; Katre, S.D.; Mandewale, M.C.; Kumbhare, R.M. New J. Chem. 2018, 42,776.
[46]	Johnson, F.E.; Hamilton, C.S. J. Am. Chem. Soc. 1949, 71,74.
[47]	Catalano, A.; Carocci, A.; Defrenza, I.; Muraglia, M.; Carrieri, A.; Bambeke, F.V.; Rosato, A.; Corbo, F.; Franchini, C. Eur. J. Med. Chem. 2013, 64,357.
[48]	Naeimi, H.; Heidarnezhad, A. Res. Chem. Intermed. 2016, 42,7855.
[49]	Bondock, S.; Fadaly, W.; Metwally, M.A. J. Sulfur Chem. 2009, 30,74.
[50]	Bhalerao, D.S.; Akamanchi, K.G. Synlett 2007,2952.
[51]	Piscitelli, F.; Ballatore, C.; Smith III, A.B. Bioorg. Med. Chem. Lett. 2010, 20,644. pmid: 19954974
[52]	Morofuji, T.; Shimizu, A.; Yoshida, J. Chem. Eur. J. 2015, 21,3211. pmid: 25641711
[53]	Joyce, L.; Evindar, G.; Batey, R.A. Chem. Commun. 2004,446.
[54]	Wang, J.; Peng, F.; Jiang, J.; Lu, Z.; Wang, L.; Bai, J.; Pan, Y. Tetrahedron Lett. 2008, 49,467.
[55]	Saha, P.; Ramana, T.; Purkait, N.; Ali, M.A.; Paul, R.; Punniyamurthy, T. J. Org. Chem. 2009, 74,8719.
[56]	Feng, E.; Huang, H.; Zhou, Y.; Ye, D.; Jiang, H.; Liu, H. J. Comb. Chem. 2010, 12,422.
[57]	Wang, R.; Yang, W.-j.; Yue, Liang., Zeng, H.-y.; Synlett 2012,1643.
[58]	Cheng, Y.; Peng, Q.; Fan, W.; Li, P. J. Org. Chem. 2014, 79,5812.
[59]	Aelterman, W.; Lang, Y.; Willemsens, B.; Vervest, I.; Leurs, S.; Knaeo, F.D. Org. Process Res. Dev. 2001, 5,467.
[60]	Inamoto, K.; Hasegawa, C.; Hiroya, K.; Doi, T. Org. Lett. 2008, 10,5147.
[61]	Joyce, L.L.; Batey, R.A. Org. Lett. 2009, 11,2792.
[62]	Inamoto, K.; Hasegawa, C.; Kawasaki, J.; Hiroya, K.; Doi, T. Adv. Synth. Catal. 2010, 352,2643.
[63]	Wang, H.; Wang, L.; Shang, J.; Li, X.; Wang, H.; Gui, J.; Lei, A. Chem. Commun. 2012, 48,76.
[64]	Shen, C.; Xia, H.; Yan, H.; Chen, X.; Ranjit, S.; Xie, X.; Tan, D.; Lee, R.; Yang, Y.; Xing, B.; Huang, K.-W.; Zhang, P.; Liu, X. Chem. Sci. 2012, 3,2388.
[65]	Wang, J.; Zong, Y.; Zhang, X.; Gao, Y.; Li, Z.; Yue, G.; Quan, Z.; Wang, X. Synlett 2014, 25,2143.
[66]	Nahakpam, L.; Chingakham, B.S.; Laitonjam, W.S. J. Heterocycl. Chem. 2015, 52,267.
[67]	Gogoi, P.; Paul, B.; Hazarika, S.; Barman, P. RSC Adv. 2015, 5,57433.
[68]	Srivastava, V.; Singh, P.K.; Singh, P.P. Croat. Chem. Acta 2015, 88,227.
[69]	Sharma, S.; Pathare, R.S.; Maurya, A.K.; Gopal, K.; Roy, T.K.; Sawant, D.M.; Pardasani, R.T. Org. Lett. 2016, 18,356. pmid: 26761401
[70]	Zeng, M.-T.; Xu, W.; Liu, M.; Liu, X.; Chang, C.-Z.; Zhu, H.; Dong, Z.-B. SynOpen 2017, 1,1.
[71]	Benedí, C.; Bravo, F.; Uriz, P.; Fernández, E.; Claver, C.; Castillόn, S. Tetrahedron Lett. 2003, 44,6073.
[72]	Kobayashi, K.; Kobayashi, A.; Murahashi, K.; Fukamachi, S. Heterocycles 2011, 83,2589.
[73]	Sahoo, S.K.; Banerjee, A.; Chakraborty, S.; Patel, B.K. ACS Catal. 2012, 2,544.
[74]	Rout, S.K.; Guin, S.; Nath, J.; Patel, B.K. Green Chem. 2012, 14,2491.
[75]	Sahoo, S.K.; Khatun, N.; Gogoi, A.; Deb, A.; Patel, B.K. RSC Adv. 2013, 3,438.
[76]	Pinapati, S.; Mandapati, U.; Tamminana, R.; Rudraraju, R. ChemistrySelect 2019, 4,254.
[77]	Ding, Q.; He, X.; Wu, J. J. Comb. Chem. 2009, 11,587. pmid: 19449803
[78]	Shen, G.; Lv, X.; Bao, W. Eur. J. Org. Chem. 2009,5897.
[79]	Qiu, J.-W.; Zhang, X.-G.; Tang, R.-Y.; Zhong, P.; Li, J.-H. Adv. Synth. Catal. 2009, 351,2319.
[80]	Guo, Y.-J.; Tang, R.-Y.; Zhong, P.; Li, J.-H. Tetrahedron Lett. 2010, 51,649.
[81]	Ding, Q.; Cao, B.; Liu, X.; Zong, Z.; Peng, Y.-Y. Green Chem. 2010, 12,1607.
[82]	Canon, R.; Ramόn, D.J.; Yus, M. J. Org. Chem. 2011, 76,654. pmid: 21175155
[83]	Sun, Y.-L.; Zhang, Y.; Cui, X.-H.; Wang, W. Adv. Synth. Catal. 2011, 353,1174.
[84]	Yang, J.; Li, P.; Wang, L. Tetrahedron 2011, 67,5543.
[85]	Xiao, R.; Hao, W.; Ai, J.; Cai, M.-Z. J. Organomet. Chem. 2012, 705,44.
[86]	Wang, R.; Chen, Z.; Yue, L.; Pan, W.; Zhao, J.-J. Tetrahedron Lett. 2012, 53,4529.
[87]	Zhang, W.; Yue, Y.; Yu, D.; Song, L.; Xu, Y.-Y.; Tian, Y.-J.; Guo, Y.-J. Adv. Synth. Catal. 2012, 354,2283.
[88]	Khatum, N.; Jamir, L.; Ganesh, M.; Patel, B.K. RSC Adv. 2012, 2,11557.
[89]	Yao, R.; Liu, H.; Wu, Y.; Cai, M. Appl. Organomet. Chem. 2013, 27,109.
[90]	Zhao, N.; Liu, L.; Wang, F.; Li, J.; Zhang, W. Adv. Synth. Catal. 2014, 356,2575.
[91]	Liu, J.; Zhang, X.; Yang, J.; Wang, L. Appl. Organomet. Chem. 2014, 28,198.
[92]	Gaddam, S.; Kasireddy, H.R.; Konkala, K.; Katla, R.; Durga, N.Y. V. Chin. Chem. Lett. 2014, 25,732.
[93]	Azizi, K.; Karimi, M.; Heydari, A. Tetrahedron Lett. 2015, 56,812.
[94]	Moghadam, F.K.; Jarrah, N.; Mashayekh-Salehi, A.; Ghanbaripour, R. Synlett 2016, 27,1665.
[95]	Chen, L.; Huang, B.; Nie, Q.; Cai, M. Appl. Organomet. Chem. 2016, 30,446.
[96]	Mishra, N.; Singh, A.S.; Agrahari, A.K.; Singh, S.K.; Singh, M.; Tiwari, V.K. ACS Comb. Sci. 2019, 21,389.
[97]	Le, Z.-G.; Xu, J.-P.; Rao, H.-Y.; Ying, M. J. Heterocycl. Chem. 2006, 43,1123.
[98]	Banerjee, A.; Santra, S.K.; Rout, S.K.; Patel, B.K. Tetrahedron 2013, 69,9096.
[99]	Xu, Y.; Li, B.; Zhang, X.; Fan, X. J. Org. Chem. 2017, 82,9637.
[100]	Wang, P.; Tang, S.; Lei, A. Green Chem. 2017, 19,2092.
[101]	He, Y.; Li, J.; Luo, S.; Huang, J.; Zhu, Q. Chem. Commun. 2016, 52,8444.
[102]	Mirza, B.; Mirzazadeh, R.; Zeeb, M. J. Chem. Res. 2013, 37,778.
[103]	Yao, G.; Wang, B.-F.; Yang, S.; Zhang, Z.-X.; Xu, H.-H.; Tang, R.-Y. RSC Adv. 2019, 9,3403.
[104]	El-Sharief, A.M. Sh.; Ammar, Y.A.; Zahran, M.A.; Sabet, H.K. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179,267.
[105]	Cee, V.J.; Downing, N.S. Tetrahedron Lett. 2006, 47,3747.
[106]	Yella, R.; Patel, B.K. J. Comb. Chem. 2010, 12,754. doi: 10.1021/cc100124q pmid: 20718465
[107]	Wang, W.; Zhong, W.; Zhou, R.; Yu, J.; Dai, J.; Ding, Q.; Peng, Y. Heterocycles 2010, 81,2841.
[108]	Ding, Q.; Cao, B.; Yang, Q.; Liu, X.; Peng, Y. Phosphorus, Sulfur Silicon Relat. Elem. 2011, 186,1782.
[109]	Zhang, X.; Jia, X.; Wang, J.; Fan, X. Green Chem. 2011, 13,413.
[110]	Sharma, R.; Bala, M.; Verma, P.K.; Singh, B. Synth. Commun. 2015, 45,2106.
[111]	Xie, Y.; Zhang, F.; Chen, X.; Li, J. Heterocycles 2010, 81,2087.
[112]	Fajkusova, D.; Pesko, M.; Keltosova, S.; Guo, J.; Oktabec, Z.; Vejsova, M.; Kollar, P.; Coffey, A.; Csollei, J.; Kralova, K.; Jampilek, J. Bioorg. Med. Chem. 2012, 20,7059.
[113]	Fajkusova, D.; Pazdera, P. Synthesis 2008,1297.
[114]	El-Faham, A.; Chebbo, M.; Abdul-Ghani, M.; Younes, G. J. Heterocycl. Chem. 2006, 43,599.
[115]	Vlaar, T.; Cioc, R.C.; Mampuys, P.; Maes, B.U. W.; Orru, R.V. A.; Ruijter, E. Angew. Chem. Int. Ed. 2012, 51,13058.
[116]	Zhu, T.-H.; Wang, S.-Y.; Wang, G.-N.; Ji, S.-J. Chem.-Eur. J. 2013, 19,5850. pmid: 23526676
[117]	Wang, G.-N.; Zhu, T.-H.; Wang, S.-Y.; Wei, T.-Q.; Ji, S.-J. Tetrahedron 2014, 70,8079.
[118]	Zhu, T.-H.; Xu, X.-P.; Cao, J.-J.; Wei, T.-Q.; Wang, S.-Y.; Ji, S.-J. Adv. Synth. Catal. 2014, 356,509.
[119]	Dumonteil, G.; Hiebel, M.-A.; Scherrmann, M.-C.; Berteina-Raboin, S. RSC Adv. 2016, 6,73517.
[120]	Min, H, Ziao, G.; Liu, W.; Liang, Y. Org. Biomol. Chem. 2016, 14,11088. doi: 10.1039/c6ob02413k pmid: 27872926
[121]	Pi, S.-S.; Zhang, X.-G.; Tang, R.-Y.; Li, J.-H. Synlett 2009,3032.
[122]	Katari, N.K.; Venkatanarayana, M.; Srinivas, K. J. Chem. Sci. 2015, 127,447.
[123]	Xu, W.; Zeng, M.-T.; Liu, M.; Liu, S.-S.; Li, Y.-S.; Dong, Z.-B. Synthesis 2017, 49,3084.
[124]	Xu, W.; Zeng, M.-T.; Liu, M.; Liu, X.; Chang, C.-Z.; Zhu, H.; Dong, Z.-B. J. Sulfur Chem. 2017, 38,644.
[125]	Ma, D.; Lu, X.; Shi, L.; Zhang, H.; Jiang, Y.; Liu, X. Angew. Chem. Int. Ed. 2011, 50,1118.
[126]	Satish, G.; Reddy, K.H. V.; Ramesh, K.; Karnakar, K.; Nageswar, Y.V. D. Tetrahedron Lett. 2012, 53,2518. doi: 10.1016/j.tetlet.2012.03.012
[127]	Zhang, Z.; Wang, F.-J.; Wu, H.-H.; Tan, Y.-J. Chem. Lett. 2015, 44,440.
[128]	Takagi, K. Chem. Lett. 1986, 15,265.
[129]	Monguchi, D.; Fujiwara, T.; Furukawa, H.; Mori, A. Org. Lett. 2009, 11,1607. pmid: 19254040
[130]	Tanba, S.; Fujiwara, T.; Monguchi, D.; Mori, A. J. Phys.: Conf. Ser. 2010, 232,012010.
[131]	Wang, Q.; Schreiber, S.L. Org. Lett. 2009, 11,5178.
[132]	Cho, S.H.; Kim, J.Y.; Lee, S.Y.; Chang, S. Angew. Chem. Int. Ed. 2009, 48,9127.
[133]	Kim, J.Y.; Cho, S.H.; Joseph, J.; Chang, S. Angew. Chem. Int. Ed. 2010, 49,9899.
[134]	Mitsuda, S.; Fujiwara, T.; Kimigafukuro, K.; Monguchi, D.; Mori, A. Tetrahedron 2012, 68,3585.
[135]	Satish, G.; Reddy, H.V.; Anil, B.S. P.; Shankar, J.; Kumar, R.U.; Nageswar, Y.V. D. Tetrahedron Lett. 2014, 55,5533.
[136]	Walczyński, K.; Guryn, R.; Zuiderveld, O.P.; Timmerman, H. Farmaco 1999, 54,684.
[137]	Charles, M.D.; Schultz, P.; Buchwald, S.L. Org. Lett. 2005, 7,3965. pmid: 16119943
[138]	Motiwala, H.F.; Kumar, R.; Chakraborti, A.K. Aust. J. Chem. 2007, 60,369.
[139]	Ramana, M.M. V.; Sharma, M.R. J. Chem. Pharm. Res. 2013, 5,122.
[140]	Toulot, S.; Heinrich, T.; Leroux, F.R. Adv. Synth. Catal. 2013,355 , 3263.
[141]	Reddy, K.H. V.; Kumar, B.S. P.; Reddy, V.P.; Kumar, R.U.; Nageswar, Y.V. D. RSC Adv. 2014, 4,45579.
[142]	Kumar, R.U.; Reddy, H.V.; Kumar, B. S., P.A.; Satish, G.; Reddy, V.P.; Nageswar, Y.V. D. Tetrahedron Lett. 2016, 57,637.
[143]	Zhu, Y.-Q.; Zhang, R.; Sang, W.; Wang, H.-J.; Wu, Y.; Yu, B.-Y.; Zhang, J.-C.; Cheng, H.; Chen, C. Org. Chem. Front. 2020, 7,1981.
[144]	Yin, J.; Zhao, M.M.; Huffman, M.A.; Mcnamara, J.M. Org. Lett. 2002, 4,3481. pmid: 12323049
[145]	Shen, Q.; Ogata, T.; Hartwig, J.F. J. Am. Chem. Soc. 2008, 130,6586. pmid: 18444639
[146]	Murthy, S.N.; Madhav, B.; Reddy, V.P.; Nageswar, Y.V. D. Adv. Synth. Catal. 2010, 352,3241.
[147]	Heo, Y.; Hyun, D.; Kumar, M.R.; Jung, H.M.; Lee, S. Tetrahedron Lett. 2012, 53,6657.
[148]	McGowan, M.A.; Henderson, J.L.; Buchwald, S.L. Org. Lett. 2012, 14,1432. pmid: 22394197
[149]	Das, R.; Mandal, M.; Chakraborty, D. Asian J. Org. Chem. 2013, 2,579.
[150]	Wang, D.; Kuang, D.; Zhang, F.; Liu, Y.; Ning, S. Tetrahedron Lett. 2014, 55,7121.
[151]	Wang, P.; Li, J.; Jiang, X.; Liu, Z.; Ye, N.; Xu, Y.; Yang, G.; Xu, Y.; Zhang, A. Tetrahedron 2014, 70,5666.
[152]	Majumder, A.; Gupta, R.; Mandal, M.; Babu, M.; Chakraborty, D. J. Organomet. Chem. 2015, 781,23.
[153]	Rao, D.N.; Rasheed, SK.; Aravinda, S.; Vishwakarma, R.A.; Das, P. RSC Adv. 2013, 3,11472.
[154]	Han, Y.; Zhang, M.; Zhang, Y.-Q.; Zhang, Z.-H. Green Chem. 2018, 20,4891.
[155]	Chand, S.; Kumar, S.; Singh, R.; Singh, K.N. ChemistrySelect 2019, 4,718.
[156]	Moser, D.; Duan, Y.; Wang, F.; Ma, Y.; O’Neil, M.J.; Cornella, J. Angew. Chem. Int. Ed. 2018, 57,11035.
[157]	Saima; Kumar, L.; Lavekar, A. G.; Sharma, T.; Shamsuzzama; Equbal, D.; Siddiqi, M. I.; Sinha, A. K.; Nazir, A. ChemistrySelect 2018, 3,3539.
[158]	Lee, E.; An, Y.; Kwon, J.; Kim, K.I.; Jeon, R. Bioorg. Med. Chem. 2017, 25,3617.
[159]	Ji, Z.; Zhou, F.; Wei, S. Bioorg. Med. Chem. Lett. 2015, 25,4065. pmid: 26318996
[160]	Ismail, M.M. F.; Abdulwahab, H.G.; Nossier, E.S.; Menofy, N.G. E.; Abdelkhalek, B.A. Bioorg. Chem. 2020, 94,103437. doi: 10.1016/j.bioorg.2019.103437 pmid: 31812260
[161]	Jian, R.-K.; Wang, P.; Duan, W.; Wang, J.; Zheng, X.; Weng, J. Ind. Eng. Chem. Res. 2016, 55,11520.
[162]	Padilla-Martínez, I.I.; González-Encarnación, J.M.; García-Báez, E.V.; Cruz, A.; Ramos-Organillo, Á.A. Molecules 2019, 24,3391.
[163]	Stewart, G.W.; Baxter, C.A.; Cleator, E.; Sheen, F.J. J. Org. Chem. 2009, 74,3229. pmid: 19317430
[164]	Zeng, W.; Dang, P.; Zhang, X.; Liang, Y.; Peng, C. RSC Adv. 2014, 4,31003.
[165]	Boddapati, S.N. M.; Kurmarayuni, C.M.; Mutchu, B.R.; Tamminana, R.; Bollikolla, H.B. Org. Biomol. Chem. 2018, 16,8267.
[166]	Castanheiro, T.; Suffert, J.; Gulea, M.; Donnard, M. Org. Lett. 2016, 18,2588. pmid: 27192105
[167]	Kumar, D.; Mishra, B.B.; Tiwari, V.K. J. Org. Chem. 2014, 79,251. pmid: 24313219
[168]	Zhao, J.; Huang, H.; Wu, W.; Chen, H.; Jiang, H. Org. Lett. 2013, 15,2604. pmid: 23662734

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

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 53

References 168

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Baochang Gao, Yu Shi, Yuan Tian, Zhiguo Zhang, Jingru Zhang, Yufeng Sun, Guoliang Mao, Lingyan Dai. Synthesis of 4-Methyl-2-oxo-6-arylamino-2H-pyran-3-carbonitrile Derivatives [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 644-649.
[2]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[3]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[4]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[5]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[6]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[7]	Jianghu Dong, Liangming Xuan, Chi Wang, Chenxi Zhao, Haifeng Wang, Qiongjiao Yan, Wei Wang, Fen'er Chen. Recent Advances in Visible-Light-Induced C(3)—H Functionalization of Quinoxalinones under Transition-Metal-Free or Photocatalyst-Free [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 111-136.
[8]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[9]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[10]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[11]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[12]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[13]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[14]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[15]	Jing Tang, Wenkun Luo, Jun Zhou. Advances in the Synthesis of Azaspiro[4.5]trienones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3006-3034.