2-取代苯并噻唑化合物的合成进展
收稿日期: 2020-07-12
修回日期: 2020-08-20
网络出版日期: 2020-09-30
基金资助
国家重大创新药物科技计划基金(2017ZX09101002-001-004); 江苏省研究生科研与实践创新计划(SJCX20_0410)
Progress in Synthesis of 2-Substituted Benzothiazole Compounds
Received date: 2020-07-12
Revised date: 2020-08-20
Online published: 2020-09-30
Supported by
Major National Science and Technology Program of China for Innovation Drug(2017ZX09101002-001-004); Postgraduate Research & Practice Innovation Program of Jiangsu Province(SJCX20_0410)
张俊 , 刘雅菲 , 张育榕 , 呼亮 , 韩世清 . 2-取代苯并噻唑化合物的合成进展[J]. 有机化学, 2021 , 41(3) : 1053 -1071 . DOI: 10.6023/cjoc202007036
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.
[1] | (a) Tebbe, M. J.; Spitzer, W. A.; Victor, F.; Miller, S. C.; Lee, C. C.; Sattelberg, T. R.; Mckinney, E.; Tang, C. J. J. Med. Chem. 1997, 40, 3937. |
[1] | (b) Zaharia, V.; Ignat, A.; Palibroda, N.; Ngameni, B.; Kuete, V.; Fokunang, C. N.; Moungang, M. L.; Ngadjui, B. T. Eur. J. Med. Chem. 2010, 45, 5080. |
[1] | (c) Hutchinson, I. S.; Jennings, A.; Vishnuvajjala, B. R.; Westwell, A. D.; Stevens, M. F. G. J. Med. Chem. 2002, 45, 744. |
[2] | (a) Katla, R.; Chowrasia, R.; Manjari, P. S.; Domingues, N. L. C. RSC Adv. 2015, 5, 41716. |
[2] | (b) Kamal, A.; Khan, M. N.; Reddy, A. K. S.; Rohini, K. Bioorg. Med. Chem. 2007, 15, 1004. |
[3] | Gan, F. Q.; Luo, P. Y.; Lin, J. Y.; Ding, Q. P. Synthesis 2020, 52, 3530. |
[4] | (a) Fajkusova, D.; Pesko, M.; Keltosova, S.; Guo, J. H.; Oktabec.; Vejsova, M.; Kollar, P.; Coffey, A.; Csollei, J.; Kralova, K.; Jampilek, J. Bioorg. Med. Chem. 2012, 20, 7059. |
[4] | (b) Kitagawa, T.; Tsutsui, C. Chem. Pharm. Bull. 2000, 48, 1363. |
[5] | Li, Y.; Wang, Y. L. Chin. J. Org. Chem. 2006, 26, 878. (in Chinese) |
[5] | (李焱, 王玉炉, 有机化学, 2006, 26, 878.) |
[6] | Hofmann, A. W. Ber. Dtsch. Chem. Ges. 1879, 12, 1126. |
[7] | (a) 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) |
[7] | (竺宁, 张志伟, 高敏, 韩利民, 索全伶, 洪海龙, 有机化学, 2013, 33, 1423.) |
[8] | Dai, X. Q.; Zhu, Y. B.; Wang, Z. Y.; Weng, J. Q. Chin. J. Org. Chem. 2017, 37, 1924. (in Chinese) |
[8] | (戴小强, 朱亚波, 汪洲洋, 翁建全, 有机化学, 2017, 37, 1924.) |
[9] | Liu, X.; Dong, Z. B. Eur. J. Org. Chem. 2020, 4, 408. |
[10] | Yang, D.; Liu, P.; Zhang, N.; Wei, W.; Yue, M. B.; You, J. M.; Wang, H. ChemCatChem 2014, 6, 3434. 7aba1095-83d1-49e6-8120-584eec782575 |
[11] | Katla, R.; Chowrasia, R.; Manjari, P. S.; Domingues, N. L. C. RSC Adv. 2015, 5, 41716. |
[12] | Ziarati, A.; Sobhani-Nasab, A.; Rahimi-Nasrabadi, M.; Ganjali, M. R.; Badiei, A. J. Rare Earths 2017, 35, 374. |
[13] | Karimian, R.; Davarpanah, S. J. Appl. Organomet. Chem. 2018, 32, 4529. |
[14] | Yang, D. S.; Zhu, X.; Wei, W.; Sun, N. N.; Yuan, L.; Jiang, M.; You, J. M.; Wang, H. RSC Adv. 2014, 4, 17832. |
[15] | Sharma, H.; Singh, N.; Jang, D. O. Green Chem. 2014, 16, 4922. |
[16] | Sharma, P.; Gupta, M.; Kant, R., Gupta, V. K. New J. Chem. 2015, 39, 5116. |
[17] | Dhopte, K. B.; Zambare, R. S.; Patwardhan, A. V.; Nemade, P. R. RSC Adv. 2016, 6, 8164. |
[18] | Draganov, A. B.; Wang, K.; Holmes, J.; Damera, K.; Wang, D. Z.; Dai, C. F.; Wang, B. H. Chem. Commun. 2015, 51, 15180. |
[19] | Wade, A. R.; Pawar, H. R.; Biware, M. V.; Chikate, R. C. Green Chem. 2015, 17, 3879. |
[20] | Jakhade, A. P.; Biware, M. V.; Chikate, R. C. ACS Omega 2017, 2, 7219. |
[21] | Chhabra, M.; Sinha, S.; Banerjee, S.; Paira, P. Bioorg. Med. Chem. Lett. 2016, 26, 213. |
[22] | Senapak, W.; Saeeng, R.; Jaratjaroonphong, J.; Sirion, U. Mol. Catal. 2018, 458, 97. |
[23] | Nguyen, Q. T.; Thi Hang, A. H.; Ho Nguyen, T. L.; Nguyen, C. D. K.; Tran, P. H. RSC Adv. 2018, 8, 11834. |
[24] | Mayo, M. S.; Yu, X. Q.; Zhou, X. Y.; Feng, X. J.; Yamamoto, Y.; Bao, M. Org. Lett. 2014, 16, 764. |
[25] | Miao, C. X.; Hou, Q.; Wen, Y. T.; Han, F.; Li, Z.; Yang, L.; Xia, C. G. ACS Sustainable Chem. Eng. 2019, 7, 12008. |
[26] | Liu, J.; Liu, Q.; Yi, H.; Qin, C.; Bai, Q. P.; Qi, X. T.; Lan, Y.; Lei, A. W. Angew. Chem., Int. Ed. 2014, 53, 502. |
[27] | To, T. A.; Vo, Y. H.; Nguyen, H. T. T.; Ha, P. T. M.; Doan, S. H.; Doan, T. L. H.; Li, S; Le, H. V.; Tu, T. N.; Phan, N. T. S. J. Catal. 2019, 370, 11. |
[28] | Wang, H. B.; Huang, J. M. Adv. Synth. Catal. 2016, 358, 1975. |
[29] | Penteado, F.; Vieira, M. M.; Perin, G.; Alves, D.; Jacob, R. G.; Santi, C.; Lenard?o, E. J. Green Chem. 2016, 18, 6675. |
[30] | Laha, J. K.; Patel, K. V.; Tummalapalli, K. S. S.; Dayal, N. Chem. Commun. 2016, 52, 10245. |
[31] | Li, Z. W.; Dong, J. Y.; Chen, X. L.; Li, Q.; Zhou, Y. B.; Yin, S. F. J. Org. Chem. 2015, 80, 9392. |
[32] | Nagao, I.; Ishizaka, T.; Kawanami, H. Green Chem. 2016, 18, 3494. |
[33] | Ray, S.; Das, R.; Banerjee, B.; Bhaumik, A.; Mukhopadhyay, C. RSC Adv. 2015, 5, 72745. |
[34] | Chen, X. L.; Chen, T. Q.; Zhou, Y. B.; Han, D. Q.; Han, L. B.; Yin, S. F. Org. Biomol. Chem. 2014, 12, 3802. |
[35] | Laha, J. K.; Tummalapalli, K. S. S.; Jethava, K. P. Org. Biomol. Chem. 2016, 14, 2473. |
[36] | Gopalaiah, K.; Chandrudu, S. N. RSC Adv. 2014, 5, 5015. |
[37] | Naresh, G.; Kant, R.; Narender, T. J. Org. Chem. 2014, 79, 3821. |
[38] | Hudwekar, A. D.; Verma, P. K.; Kour, J.; Balgotra, S.; Sawant, S. D. Eur. J. Org. Chem. 2019, 25, 1242. |
[39] | Kazi, I.; Sekar, G. Org. Biomol. Chem. 2019, 17, 9743. |
[40] | Ramachandran, R.; Prakash, G.; Selvamurugan, S.; Viswanathamurthi, P.; Malecki, J. G.; Ramkumar, V. Dalton Trans. 2014, 43, 7889. |
[41] | Lai, Y. L.; Ye, J. S.; Huang, J. M. Chem.-Eur. J. 2016, 22, 5425. |
[42] | Wang, D. K.; Albero, J.; García, H.; Li, Z. H. J. Catal. 2017, 349, 156. |
[43] | Shi, X. K.; Guo, J. M.; Liu, J. P.; Ye, M. D.; Xu, Q. Chem.-Eur. J. 2015, 21, 9988. |
[44] | Das, K.; Mondal, A.; Srimani, D. Chem. Commun. 2018, 54, 10582. |
[45] | Zhang, J. L.; Qiao, M. J.; Chen, L.; Dong, Y. B.; Jiao, C. K.; Liao, S. Q.; Wu, Y. J. Org. Chem. Front. 2019, 6, 2844. |
[46] | He, K. H.; Tan, F. F.; Zhou, C. Z.; Zhou, G. J.; Yang, X. L.; Li, Y. Angew. Chem., Int. Ed. 2017, 56, 3080. |
[47] | Wu, Y.; Yi, H.; Lei, A. W. ACS Catal. 2018, 8, 1192. |
[48] | Maier, A. F. G.; Tussing, S.; Schneider, T.; Fl?rke, U.; Qu, Z. W.; Grimme, S.; Paradies, J. Angew. Chem., Int. Ed. 2016, 55, 12219. |
[49] | Peng, B.; Nie, Y. Chin. Sci. Technol. Terms. 2010, 12, 44. (in Chinese) |
[49] | (彭斌, 聂永, 中国科技术语, 2010, 12, 44.) d5e44edf-4845-497e-a822-a6f4977cb8df |
[50] | Kojima, M.; Kanai, M. Angew. Chem., Int. Ed. 2016, 55, 12224. |
[51] | Hati, S.; Sen, S. Eur. J. Org. Chem. 2017, 9, 1277. |
[52] | Zhong, J. J.; To, W. P.; Liu, Y.G; Lu, W.; Che, C. M. Chem. Sci. 2019, 10, 4883. |
[53] | Nguyen, T. B.; Ermolenko, L.; Retailleau, P.; Al-Mourabit, A. Angew. Chem., Int. Ed. 2014, 53, 13808. |
[54] | Nguyen, T. B.; Ermolenko, L.; Corbin, M.; Al-Mourabit, A. Org. Chem. Front. 2014, 1, 1157. |
[55] | Pan, L.; Yu, L. T.; Wu, Z. Q.; Li, Z. K.; Xiang, H. F.; Zhou, X. G. RSC Adv. 2014, 4, 27775. |
[56] | Guntreddi, T.; Vanjari, R.; Singh, K. N. Org. Lett. 2015, 17, 976. |
[57] | Nguyen, L. A.; Ngo, Q. A.; Retailleau, P.; Nguyen, T. B. Green Chem. 2017, 19, 4289. |
[58] | Ma, X. T.; Yu, L.; Su, C. L.; Yang, Y. Q.; Li, H.; Xu, Q. Adv. Synth. Catal. 2017, 359, 1649. |
[59] | Li, G. Z.; Jiang, J. J.; Zhang, F.; Xiao, F. H.; Deng, G. J. Org. Biomol. Chem. 2017, 15, 10024. |
[60] | Jiang, J. J.; Li, G. Z.; Zhang, F.; Xie, H.; Deng, G. J. Adv. Synth. Catal. 2018, 360, 1622. |
[61] | Huang, Y. B.; Zhou, P. Q.; Wu, W. Q.; Jiang, H. F. J. Org. Chem. 2018, 83, 2460. |
[62] | Huang, Y. B.; Yan, D. H.; Wang, X.; Zhou, P. Q.; Wu, W. Q.; Jiang, H. F. Chem. Commun. 2018, 54, 1742. |
[63] | Xing, Q. Y.; Ma, Y. F.; Xie, H.; Xiao, F. H.; Zhang, F.; Deng, G. Z. J. Org. Chem. 2019, 84, 1238. |
[64] | Zhang, J.; Zhao, X.; Liu, P.; Sun, P. P. J. Org. Chem. 2019, 84, 12596. |
[65] | Tong, Y.; Pan, Q.; Jiang, Z. Q.; Miao, D. Z.; Shi, X. S.; Han, S Q. Tetrahedron Lett. 2014, 55, 54993. |
[66] | Gan, H. F.; Miao, D. Z.; Pan, Q.; Hu, R. H.; Li, X. T.; Han, S. Q. Chem.-Asian J. 2016, 11, 1770. |
[67] | Yang, Z.; Hu, R. H.; Li, X. T.; Wang, X.; Gu, R.; Han, S. Q. Tetrahedron Lett. 2017, 58, 2366. |
[68] | Wang, X.; Miao, D. Z.; Li, X. T.; Hu, R. H.; Yang, Z.; Gu, R.; Han, S. Q. Tetrahedron 2017, 73, 5194. |
[69] | Wang, X.; Li, X. T.; Hu, R. H.; Yang, Z.; Gu, R.; Ding, S.; Li, P. Y.; Han, S. Q. Synlett 2018, 29, 219. |
[70] | Gao, Y. Y.; Song, Q. L.; Cheng, G. L.; Cui, X. L. Org. Biomol. Chem. 2014, 12, 1044. |
[71] | Huang, C.; Wu, J.; Song, C. J.; Ding, R.; Qiao, Y.; Hou, H. W.; Chang, J. B.; Fan, Y. T. Chem. Commun. 2015, 51, 10353. |
[72] | Yang, P.; Wang, R.; Wu, H.; Du, Z. Y.; Fu, Y. Asian J. Org. Chem. 2017, 6, 184. |
[73] | Dai, W. C.; Wang, Z. X. Org. Chem. Front. 2017, 4, 1281. |
[74] | Matsushita, K.; Takise, R.; Hisada, T.; Suzuki, S.; Isshiki, R.; Itami, K.; Muto, K.; Yamaguchi, J. Chem.-Asian J. 2018, 13, 2393. |
[75] | Liu, K. M.; Liao, L. Y.; Duan, X. F. Chem. Commun. 2015, 51, 1124. |
[76] | Liu, C.; Wang, Q. Org. Lett. 2016, 18, 5118. |
[77] | Li, S.; Wan, P.; Ai, J.; Sheng, R.; Hu, Y. Z.; Hu, Y. H. Adv. Synth. Catal. 2017, 359, 772. |
[78] | Zhou, P. X.; Shi, S.; Wang, J.; Zhang, Y. L.; Li, C. Z.; Ge, C. P. Org. Chem. Front. 2019, 6, 1942. |
[79] | Yang, F. Z.; Koeller, J.; Ackermann, L. Angew. Chem., Int. Ed. 2016, 55, 4759. |
[80] | Balsane, K. E.; Gund, S. H.; Nagarkar, J. M. Catal. Commun. 2017, 89, 29. |
[81] | Tran, P.; Hang, A. -H. T. RSC Adv. 2018, 8, 11127. |
[82] | Ji, W.; Wang, H.; Li, C. A.; Gao, F.; An, Z. F.; Huang, L.; Wang, H.; Pan, Y.; Zhu, D. R.; Wang, J. Q.; Guo, C.; Mayoral, J. A.; Jing, S. J. Catal. 2019, 378, 270. |
[83] | Ogiwara, Y.; Iino, Y.; Sakai, N. Chem.-Eur. J. 2019, 25, 6513. |
[84] | Cheng, Y. N.; Peng, Q.; Fan, W. G.; Li, P. X. J. Org. Chem. 2014, 79, 5812. |
[85] | Alla, S. K.; Sadhu, P.; Punniyamurthy, T. J. Org. Chem. 2014, 79, 7502. |
[86] | Zhang, G. T.; Liu, C.; Yi, H.; Meng, Q. Y.; Bian, C. L.; Chen, H.; Jian, J. X.; Wu, L. Z.; Lei, A. W. J. Am. Chem. Soc. 2015, 137, 9273. |
[87] | Qian, X. Y.; Li, S. Q.; Song, J. S.; Xu, H. C. ACS Catal. 2017, 7, 2730. |
[88] | Wang, P.; Tang, S.; Lei, A. W. Green Chem. 2017, 19, 2092. |
[89] | Folgueiras-Amador, A. A.; Qian, X. Y.; Xu, H. C.; Wirth, T. Chem.-Eur. J. 2018, 24, 487. |
[90] | Mishra, N.; Singh, A. S.; Agrahari, A. K.; Singh, S. K.; Singh, M.; Tiwari, V. K. ACS Comb. Sci. 2019, 21, 389. |
[91] | Xu, Z. M.; Li, H. X.; Young, D. J.; Zhu, D. L.; Li, H. Y.; Lang, J. P. Org. Lett. 2019, 21, 237. |
[92] | Zhang, X. Y.; Zeng, W. L.; Yang, Y.; Huang, H.; Liang, Y. Org. Lett. 2014, 16, 876. |
[93] | Duan, F. F.; Song, S. Q.; Xu, R. S. Chem. Commun. 2017, 53, 2737. |
[94] | Yang, W. C.; Wei, K.; Sun, X.; Zhu, J.; Wu, L. Org. Lett. 2018, 20, 3144. |
[95] | Natarajan, P.; Muskan, M.; Brar, N. K.; Kaur, J. J. Org. Chem. Front. 2018, 5, 1527. |
[96] | Luo, K.; Yang, W. C.; Wei, K.; Liu, Y.; Wang, J. K.; Wu, L. Org. Lett. 2019, 21, 7851. |
[97] | Ramachandran, R.; Prakash, G.; Selvamurugan, S.; Viswanathamurthi, P.; Malecki, J. G.; Ramkumar, V. Dalton Trans. 2014, 43, 7889. |
[98] | Li, S. Y.; Li, X. H.; Yuan, Q. C.; Shi, X. K.; Xu, Q. Green Chem. 2015, 17, 3260. |
[99] | Rajaguru, K.; Mariappan, A.; Manjusri, R.; Muthusubramanian, S.; Bhuvanesh, N. RSC Adv. 2015, 5, 86832. |
[100] | Lin, W. H.; Wu, W. C.; Selvaraju, M.; Sun, C. M. Org. Chem. Front. 2017, 4, 392. |
/
〈 |
|
〉 |