A New Method for the Synthesis of 2-Arylbenzothiazoles Oxidized by Selectfluor

doi:10.6023/cjoc202105010

Abstract

2-Arylbenzothiazoles were effectively synthesized via an oxidative process by Selectfluor in 1-butanol at 120 ℃, using 2-arylbenzothiazoles and aryl/aliphatic ketones as starting materials. Bioactive pharmaceutical intermediates were obtained by selecting substituents on the ring of aryl methyl ketones.

Key words: Selectfluor, 2-arylbenzothiazole, aryl methyl ketone, 2-aminobenzenethiol, oxidation

Cite this article

Qinjiao Fu, Ruiqin Zhang, Huanyi Qiu, Renchao Ma, Yongmin Ma. A New Method for the Synthesis of 2-Arylbenzothiazoles Oxidized by Selectfluor[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3585-3592.

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References 20

[1]	(a) Zablotskaya, A.; Segal, I.; Geronikaki, A.; Eremkina, T.; Belyakov, S.; Petrova, M.; Shestakova, I.; Zvejniece, L.; Nikolajeva, V. Eur. J. Med. Chem. 2013, 70, 846. doi: 10.1016/j.ejmech.2013.10.008 pmid: 24262377
	(b) Cai, J.; Sun, M.; Wu, X.; Chen, J.; Wang, P.; Zong, X.; Ji, M. Eur. J. Med. Chem. 2013, 63, 702. doi: 10.1016/j.ejmech.2013.03.013 pmid: 24262377
	(c) Huang, S.-T.; Hsei, I. J.; Chen, C. Bioorg. Med. Chem. 2006, 14, 6106. doi: 10.1016/j.bmc.2006.05.007 pmid: 24262377
[2]	(a) Diao, P.-C.; Lin, W.-Y.; Jian, X.-E.; Li, Y.-H.; You, W.-W.; Zhao, P.-L. Eur. J. Med. Chem. 2019, 179, 196. doi: 10.1016/j.ejmech.2019.06.055
	(b) Racane, L.; Pticek, L.; Fajdetic, G.; Tralic-Kulenovic, V.; Klobucar, M.; Pavelic, S. K.; Peric, M.; Paljetak, H. C.; Verbanac, D.; Starcevic, K. Bioorg. Chem. 2019, 95, 103537. doi: 10.1016/j.bioorg.2019.103537
	(c) Li, E.; Meng, Y.; Zhang, L.; Zhang, Y.; Zhou, R.; Liu, L.; Li, N.; Xin, J.; Zheng, J.; Shan, L.; Liu, H.; Zhang, Q. Chin. J. Org. Chem. 2020, 40, 417. (in Chinese). doi: 10.6023/cjoc201907016
	( 李二冬, 孟娅琪, 张路野, 张洋, 周蕊, 刘丽敏, 栗娜, 辛景超, 郑甲信, 单丽红, 刘宏民, 张秋荣, 有机化学, 2020, 40, 417.)
[3]	(a) Keri, R. S.; Patil, M. R.; Patil, S. A.; Budagumpi, S. Eur. J. Med. Chem. 2015, 89, 207. doi: 10.1016/j.ejmech.2014.10.059
	(b) Sumit, K. A.; Kumar, A.; Mishra, A. K. Mini-Rev. Med. Chem. 2020, 21, 314. doi: 10.2174/1389557520666200820133252
[4]	(a) Huang, X.; Meggers, E. Acc. Chem. Res. 2019, 52, 833. doi: 10.1021/acs.accounts.9b00028
	(b) Lu, H.-Y.; Barve, I. J.; Selvaraju, M.; Sun, C.-M. ACS Comb. Sci. 2020, 22, 42. doi: 10.1021/acscombsci.9b00161
	(c) Huo, X.; Li, W.; Zhang, B.; Chen, X.; Zhou, Y.; Zhang, J.; Han, X.; Dai, B. Chin. J. Org. Chem. 2018, 38, 3356. (in Chinese). doi: 10.6023/cjoc201805053
	( 霍新玉, 李文斌, 张博雅, 陈晓飞, 周月婷, 张洁, 韩小强, 代斌, 有机化学, 2018, 38, 3356.)
	(d) Jiang, K.; Cao, L.; Hao, Z.; Chen, M.; Cheng, J.; Li, X.; Xiao, P.; Chen, L.; Wang, Z. Chin. J. Org. Chem. 2017, 37, 2221. (in Chinese). doi: 10.6023/cjoc201703041
	( 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.)
	(e) Gabr, M. T.; El-Gohary, N. S.; El-Bendary, E. R.; El-Kerdawy, M. M.; Ni, N. Chin. Chem. Lett. 2016, 27, 380. doi: 10.1016/j.cclet.2015.12.033
[5]	(a) Guria, U. N.; Gangopadhyay, A.; Ali, S. S.; Maiti, K.; Samanta, S. K.; Manna, S.; Ghosh, A. K.; Uddin, M. R.; Mandal, S.; Mahapatra, A. K. Anal. Methods 2019, 11, 5447. doi: 10.1039/C9AY01622H
	(b) Maliyappa, M. R.; Keshavayya, J.; Mahanthappa, M.; Shivaraj, Y.; Basavarajappa, K. V. J. Mol. Struct. 2020, 1199, 126959. doi: 10.1016/j.molstruc.2019.126959
[6]	(a) Zhang, F.; Xu, J.; Guo, X.; Yuan, B.; Huang, H.; Li, L. Appl. Surf. Sci. 2020, 501, 144054. doi: 10.1016/j.apsusc.2019.144054
	(b) Devi, A. S.; Aswathy, V. V.; Mary, Y. S.; Panicker, C. Y.; Armakovic, S.; Armakovic, S. J.; Ravindran, R.; Van Alsenoy, C. J. Mol. Struct. 2017, 1148, 282. doi: 10.1016/j.molstruc.2017.07.065
	(c) Dzulkharnien, N. S. F.; Salleh, N. M.; Yahya, R.; Karim, M. R. Soft Mater. 2017, 15, 292. doi: 10.1080/1539445X.2017.1355816
[7]	Wang, Y.; Zhou, R.; Liu, W.; Liu, C.; Wu, P. Chin. Chem. Lett. 2020, 31, 2950. doi: 10.1016/j.cclet.2020.01.023
[8]	(a) Zhang, J.; Liu, Y.; Zhang, Y.; Hu, L.; Han, S. Chin. J. Org. Chem. 2021, 41, 1053. (in Chinese). doi: 10.6023/cjoc202007036
	( 张俊, 刘雅菲, 张育榕, 呼亮, 韩世清, 有机化学, 2021, 41, 1053.)
	(b) Dai, X.; Zhu, Y.; Wang, Z.; Weng, J. Chin. J. Org. Chem. 2017, 37, 1924. (in Chinese). doi: 10.6023/cjoc201703034
	( 戴小强, 朱亚波, 汪洲洋, 翁建全, 有机化学, 2017, 37, 1924.)
	(c) Zhu, N.; Zhang, Z.; Gao, M.; Han, L.; Suo, Q.; Hong, H. Chin. J. Org. Chem. 2013, 33, 1423. (in Chinese). doi: 10.6023/cjoc201212014
	( 竺宁, 张志伟, 高敏, 韩利民, 索全伶, 洪海龙, 有机化学, 2013, 33, 1423.)
	(d) Yang, W.; Li, B.; Zhang, M.; Wang, S.; Ji, Y.; Dong, S. Chin. Chem. Lett. 2020, 31, 1313. doi: 10.1016/j.cclet.2019.10.022
	(e) Wan, J.-P.; Zhou, Y.; Liu, Y.; Sheng, S. Green Chem. 2016, 18, 402. doi: 10.1039/C5GC01821H
	(f) Singh, M.; Vaishali, Paul, A. K.; Singh, V. Org. Biomol. Chem. 2020, 18, 4459. doi: 10.1039/D0OB00888E
[9]	(a) Ferlin, F.; van der Hulst, M. K.; Santoro, S.; Lanari, D.; Vaccaro, L. Green Chem. 2019, 21, 5298. doi: 10.1039/C9GC01641D
	(b) Fan, L.-Y.; Shang, Y.-H.; Li, X.-X.; Hua, W.-J. Chin. Chem. Lett. 2015, 26, 77. doi: 10.1016/j.cclet.2014.10.017
	(c) Samanta, S.; Das, S.; Biswas, P. J. Org. Chem. 2013, 78, 11184. doi: 10.1021/jo401445j
	(d) Mali, J. K.; Mali, D. A.; Telvekar, V. N. Tetrahedron. Lett. 2016, 57, 2324. doi: 10.1016/j.tetlet.2016.04.058
	(e) Nagao, I.; Ishizaka, T.; Kawanami, H. Green Chem. 2016, 18, 3494. doi: 10.1039/C6GC01195K
	(f) Sun, Y.; Jiang, H.; Wu, W.; Zeng, W.; Wu, X. Org. Lett. 2013, 15, 1598. doi: 10.1021/ol400379z
	(g) Ma, R.; Ding, Y.; Chen, R.; Wang, Z.; Wang, L.; Ma, Y. J. Org. Chem. 2021, 86, 310. doi: 10.1021/acs.joc.0c02095
	(h) Sharma, H.; Singh, N.; Jang, D. O, Green Chem. 2014, 16, 4922. doi: 10.1039/C4GC01142B
	(i) Li, Z.; Dong, J.; Chen, X.; Li, Q.; Zhou, Y.; Yin, S.-F. J. Org. Chem. 2015, 80, 9392. doi: 10.1021/acs.joc.5b00937
	(j) Liu, J.; Wang, C.; Ma, X.; Shi, X.; Wang, X.; Li, H.; Xu, Q. Catal. Lett. 2016, 146, 2139. doi: 10.1007/s10562-016-1818-2
	(k) Shi, X.; Guo, J. Liu, J.; Ye, M.; Xu, Q. Chem.-Eur. J. 2015, 21, 9988. doi: 10.1002/chem.201501184
[10]	(a) Xu, Y.; Li, B.; Zhang, X.; Fan, X. J. Org. Chem. 2017, 82, 9637. doi: 10.1021/acs.joc.7b01683 pmid: 30943366
	(b) Mishra, N.; Singh, A. S.; Agrahari, A. K.; Singh, S. K.; Singh, M.; Tiwari, V. K. ACS Comb. Sci. 2019, 21, 389. doi: 10.1021/acscombsci.9b00004 pmid: 30943366
	(c) Urzúa, J. I.; Contreras, R.; Salas, C. O.; Tapia, R. A. RSC Adv. 2016, 6, 82401. doi: 10.1039/C6RA18510J pmid: 30943366
[11]	Ma, D.; Xie, S.; Xue, P.; Zhang, X.; Dong, J.; Jiang, Y. Angew. Chem., Int. Ed. 2009, 48, 4222. doi: 10.1002/anie.v48:23
[12]	(a) Zhu, Y.-P.; Jia, F.-C.; Liu, M.-C.; Wu, A.-X. Org. Lett. 2012, 14, 4414. doi: 10.1021/ol301921t
	(b) Zhu, Y.-P.; Lian, M.; Jia, F.-C.; Liu, M.-C.; Yuan, J.-J.; Gao, Q.-H.; Wu, A.-X. Chem. Commun. 2012, 48, 9086. doi: 10.1039/c2cc34561g
[13]	(a) Liao, Y.; Qi, H.; Chen, S.; Jiang, P.; Zhou, W.; Deng, G.-J. Org. Lett. 2012, 14, 6004. doi: 10.1021/ol302902e
	(b) Wang, J.; Zhang, X.-Z.; Chen, S.-Y.; Yu, X.-Q. Tetrahedron 2014, 70, 245. doi: 10.1016/j.tet.2013.11.078
	(c) Liu, S.; Chen, R.; Chen, H.; Deng, G.-J. Tetrahedron Lett. 2013, 54, 3838.
[14]	(a) Yu, X.-Y.; Chen, J.-R.; Xiao, W.-J. Chem. Rev. 2021, 121, 506. doi: 10.1021/acs.chemrev.0c00030
	(b) Wan, J.-P.; Gao, Y.; Wei, L. Chem.-Asian J. 2016, 11, 2092. doi: 10.1002/asia.v11.15
	Gan, L.; Yu, Q.; Liu, Y.; Wan, J.-P. J. Org. Chem. 2021, 86, 1231. doi: 10.1021/acs.joc.0c02431
	(d) Gan, Y.; Zhang, N.; Huang, S.; Liu, Y. Chin. J. Chem. 2020, 38, 1686. doi: 10.1002/cjoc.v38.12
	(e) Wang, G.; Guo, Y.; Wan, J. Chin. J. Org. Chem. 2020, 40, 645. (in Chinese). doi: 10.6023/cjoc201912018
	( 王国栋, 郭艳辉, 万结平, 有机化学, 2020, 40, 645.)
[15]	(a) Nyffeler, P. T.; Duron, S. G.; Burkart, M. D.; Vincent, S. P.; Wong, C.-H. Angew. Chem.,Int. Ed. 2004, 44, 192. doi: 10.1002/anie.200400648
	(b) Syvret, R. G.; Butt, K. M.; Nguyen, T. P.; Bulleck, V. L.; Rieth, R. D. J. Org. Chem. 2002, 67, 4487. doi: 10.1021/jo020053u
[16]	Lv, Y.; Sun, K.; Pu, W.; Mao, S.; Li, G.; Niu, J.; Chen, Q.; Wang, T. RSC Adv. 2016, 6, 93486. doi: 10.1039/C6RA22653A
[17]	Zhao, J.; Xiao, Q.; Chen, J.; Xu, J. Eur. J. Org. Chem. 2020, 2020, 5201. doi: 10.1002/ejoc.v2020.32
[18]	Wang, H.; Ren, S.; Zhang, J.; Zhang, W.; Liu, Y. J. Org. Chem. 2015, 80, 6856. doi: 10.1021/acs.joc.5b00857
[19]	(a) Shah, S.; Arshia; Javaid, K.; Zafar, H.; Khan, K. M.; Khalil, R.; Ul-Haq, Z.; Perveen, S.; Choudhary, M. I. Bioorg. Chem. 2018, 78, 269. doi: 10.1016/j.bioorg.2018.02.013 pmid: 31698294
	(b) Ghannam, I. A. Y.; Abd El-Meguid, E. A.; Ali, I. H.; Sheir, D. H.; El Kerdawy, A. M. Bioorg. Chem. 2019, 93, 103373. doi: S0045-2068(19)31378-1 pmid: 31698294
[20]	(a) Deligeorgiev, T. G.; Kaloyanova, S.; Vasilev, A.; Vaquero, J. J., Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 2292. pmid: 18947183
	(b) Fawzia, A. Q.; Ramadan, A. M.; Kamal, U. S. Molecules 2008, 13, 2908. doi: 10.3390/molecules13112908 pmid: 18947183
	(c) Kiyofumi, I.; Chisa, H.; Kou, H.; Takayuki, D. Org. Lett. 2008, 10, 5147. doi: 10.1021/ol802033p pmid: 18947183
	(d) Wang, Z.; Tang, R.; Li, J. Chin. J. Chem. 2011, 29, 314. doi: 10.1002/cjoc.201190084 pmid: 18947183
	(e) Das, K.; Mondal, A.; Srimani, D. Chem. Commun. 2018, 54, 10582. doi: 10.1039/C8CC05877F pmid: 18947183
	(f) Xu, Z.-M.; Li, H.-X.; Young, D. J.; Zhu, D.-L.; Li, H.-Y.; Lang, J.-P. Org. Lett. 2019, 21, 237. doi: 10.1021/acs.orglett.8b03679 pmid: 18947183
	(g) Song, Q.; Feng, Q.; Zhou, M. Org. Lett. 2013, 15, 5990. doi: 10.1021/ol402871f pmid: 18947183

Entry	Product	Ar	R¹	Yield/%
1	3aa	C₆H₅	H	75 (72^b)
2	3ba	2-MeOC₆H₄	H	75
3	3ca	2-ClC₆H₄	H	73
4	3da	3-MeOC₆H₄	H	68
5	3ea	3-ClC₆H₄	H	60
6	3fa	4-ClC₆H₄	H	62
7	3ga	4-CH₃C₆H₄	H	78
8	3ha	4-NH₂C₆H₄	H	73
9	3ia	3,5-(CH₃O)₂C₆H₃	H	73
10	3ja	3,4-(CH₃)₂C₆H₃	H	76
11	3ka	3,5-F₂C₆H₃	H	70
12	3la	2,4-(CH₃)₂C₆H₃	H	65
13	3ma	3-MeO-4-HO-C₆H₃	H	56
14	3na	4-O₂NC₆H₄	H	0
15	3oa	2-Thienyl	H	58
16	3pa	2-Benzothienyl	H	55
17	3qa	2-Benzofuryl	H	40
18	3ra	2-Naphthyl	H	60
19	3sa	4-CF₃C₆H₄	H	74
20	3ab	C₆H₅	5-Cl	79
21	3eb	4-FC₆H₄	5-Cl	75
22	3fb	4-MeOC₆H₄	5-Cl	66
23	3kb	3,5-F₂C₆H₃	5-Cl	78
24	3lb	2,4-(CH₃)₂C₆H₃	5-Cl	70
25	3mb	3-MeO-4-HO-C₆H₃	5-Cl	67

Entry	Product	Ar	R¹	Yield/%
1	3aa	C₆H₅	H	75 (72^b)
2	3ba	2-MeOC₆H₄	H	75
3	3ca	2-ClC₆H₄	H	73
4	3da	3-MeOC₆H₄	H	68
5	3ea	3-ClC₆H₄	H	60
6	3fa	4-ClC₆H₄	H	62
7	3ga	4-CH₃C₆H₄	H	78
8	3ha	4-NH₂C₆H₄	H	73
9	3ia	3,5-(CH₃O)₂C₆H₃	H	73
10	3ja	3,4-(CH₃)₂C₆H₃	H	76
11	3ka	3,5-F₂C₆H₃	H	70
12	3la	2,4-(CH₃)₂C₆H₃	H	65
13	3ma	3-MeO-4-HO-C₆H₃	H	56
14	3na	4-O₂NC₆H₄	H	0
15	3oa	2-Thienyl	H	58
16	3pa	2-Benzothienyl	H	55
17	3qa	2-Benzofuryl	H	40
18	3ra	2-Naphthyl	H	60
19	3sa	4-CF₃C₆H₄	H	74
20	3ab	C₆H₅	5-Cl	79
21	3eb	4-FC₆H₄	5-Cl	75
22	3fb	4-MeOC₆H₄	5-Cl	66
23	3kb	3,5-F₂C₆H₃	5-Cl	78
24	3lb	2,4-(CH₃)₂C₆H₃	5-Cl	70
25	3mb	3-MeO-4-HO-C₆H₃	5-Cl	67

Selectfluor氧化合成2-芳基苯并噻唑的新方法