Visible-Light-Induced Cycloaddition Involving N-Propargylanilines with Arylsulfonylhydrazides: Rapid Access to 3-Sulfonated Quinoline Derivatives without Base and Catalyst

doi:10.6023/cjoc202002007

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 2078-2085.DOI: 10.6023/cjoc202002007 Previous Articles Next Articles

Special Issue: 有机光催化虚拟合辑

可见光促进N-苯丙炔胺与磺酰肼的环化:在无碱和催化剂下快速合成3-磺酰基喹啉衍生物

彭美^a, 郑扬帆^a, 黄浩^b, 叶佳^a, 邓兴国^c, 何纯莲^a

a 湖南师范大学药学院小分子靶向药物研究与创制湖南省重点实验室长沙 410081;
b 宜春学院化学与生物工程学院江西宜春 336000;
c 湖南食品药品职业学院长沙 410081

收稿日期:2020-02-06 修回日期:2020-03-25 发布日期:2020-04-13
通讯作者: 邓兴国, 何纯莲 E-mail:chunlianhe6688@163.com;734411927@qq.com
基金资助:
国家自然科学基金（Nos.21176063，81803720）、湖南省自然科学基金（（Nos.18JJ5018，2019JJ50383）、小分子靶向药物研究与创制湖南省重点实验室开放基金（No.2019CG06）资助项目.

Visible-Light-Induced Cycloaddition Involving N-Propargylanilines with Arylsulfonylhydrazides: Rapid Access to 3-Sulfonated Quinoline Derivatives without Base and Catalyst

Peng Mei^a, Zheng Yangfan^a, Huang Hao^b, Ye Jia^a, Deng Xingguo^c, He Chunlian^a

a Key Laboratory of Study and Discovery of Small Targeted Molecules of Hunan Province, School of Medicine, Hunan Normal University, Changsha 410081;
b School of Chemistry and Bioengineering, Yichun University, Yichun, Jiangxi 336000;
b Hunan Food and Drug Vocational College, Changsha 410081

Received:2020-02-06 Revised:2020-03-25 Published:2020-04-13
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21176063, 81803720), the Hunan Provincial Natural Science Foundation (Nos. 18JJ5018, 2019JJ50383), and the Department of Science and Technology Foundation of Changsha City (Nos. kq1706047, kq1801038), and the Key Laboratory of Study and Discovery of Small Targeted Molecules of Hunan Province (No. 2019CG06).

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Abstract

A visible-light-induced oxidative cyclization of N-propargylanilines with arylsulfonylhydrazides was developed using tert-butyl hydroperoxide as oxidant. This transformation offers a straightforward route to 3-sulfonated quinoline derivatives with good functional group tolerance, good to excellent yields and high regio-selectivity.

Key words: visible-light, arylsulfonylhydrazides, 3-sulfonated quinoline derivatives, regio-selectivity

Cite this article

Peng Mei, Zheng Yangfan, Huang Hao, Ye Jia, Deng Xingguo, He Chunlian. Visible-Light-Induced Cycloaddition Involving N-Propargylanilines with Arylsulfonylhydrazides: Rapid Access to 3-Sulfonated Quinoline Derivatives without Base and Catalyst[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2078-2085.

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[1] (a) Michael, J. P. Nat. Prod. Rep. 2000, 17, 603.
(b) Strekowski, L.; Say, M.; Henary, M.; Ruiz, P.; Manzel, L. Macfarlane, D. E.; Bojarski, A. J. J. Med. Chem. 2003, 46, 1242.
(c) Twin, H.; Batey, R. A. Org. Lett. 2004, 6, 4913.
(d) Michael, J. P. Nat. Prod. Rep. 2008, 25, 166.
(e) Hayat, F.; Moseley, E.; Salahuddin, A.; Van Zyl, R. L.; Azam, A. Eur. J. Med. Chem. 2011, 46, 1897.
(f) Chung, P.-Y.; Bian, Z.-X.; Pun, H.-Y.; Chan, D.; Chan, S.-C.; Chui, C.-H.; Tang, J. C.-O.; Lam, K.-H. Future Med. Chem. 2015, 7, 947.
(g) Andries, K.; Verhasselt, P.; Guillemont, J.; Göhlmann, H. W. H.; Neefs, J.-M.; Winkler, H.; Van Gestel, J.; Timmerman, P.; Zhu, M.; Lee, E.; Williams, P.; de Chaffoy, D.; Huitric, E.; Hoffner, S.; Cambau, E.; Truffot-Pernot, C.; Lounis, N.; Jarlier, V. Science 2005, 307, 223.
(h) Sun, M.; Jiang, J.; Chen, J.; Yang, Q.; Yu, X. Y. Tetrahedron 2019, 75, 130456.
(i) Xie, L.-Y.; Fang, T.-G.; Tan, J.-X.; Zhang, B.; Cao, Z.; Yang, L.-H.; He, W.-M. Green Chem. 2019, 21, 3858. (j) Cao, Z.; Zhu, Q.; Lin, Y.-W.; He, W.-M. Chin. Chem. Lett. 2019, 30, 2132.
(k) Peng, S.; Song, Y.-X.; He, J.-Y.; Tang, S.-S.; Tan, J.-X.; Cao, Z.; Lin, Y.-W.; He, W.-M. Chin. Chem. Lett. 2019, 30, 2287.
(l) Wang, L. L.; Bao, P. L.; Liu, W. W.; Liu, S. T.; Hu, C. S.; Yue, H. L.; Yang, D. S.; Wei, W. Chin. J. Org. Chem. 2018, 38, 3189(in Chinese). (王雷雷, 鲍鹏丽, 刘维伟, 刘思彤, 胡昌松, 岳会兰, 杨道山, 魏伟, 有机化学, 2018, 38, 3189.)
(m) Ye, J.-L.; Zhu, Y.-N.; Geng, H.; Huang, P.-Q. Sci. China Chem. 2018, 61, 687.
(n) Bao, P.; Wang, L.; Liu, Q.; Yang, D.; Wang, H.; Zhao, X.; Yue, H.; Wei, W. Tetrahedron Lett. 2019, 60, 214.
(o) Wang, L.; Zhang, M.; Zhang, Y.; Liu, Q.; Zhao, X.; Li, J.-S.; Luo, Z.; Wei, W. Chin. Chem. Lett. 2020, 31, 67.
[2] (a) Galambos, J.; Domány, G.; Nógrádi, K.; Wágner, G.; Keserű, G. M.; Bobok, A.; Kolok, S.; Mikó-Bakk, M. L.; Vastag, M.; Sághy, K.; Kóti, J.; Szakács, Z.; Béni, Z.; Gál, K.; Szombathelyi, Z.; Greiner, I. Biorg. Med. Chem. Lett. 2016, 26, 1249.
(b) Codony, X.; Vela, J. M.; Ramírez, M. J. Curr. Opin. Pharm. 2011, 11, 94.
(c) Zajdel, P.; Marciniec, K.; Maślankiewicz, A.; Paluchowska, M.; Satała, H. G.; Partyka, A.; Jastrzębska-Więsek, M.; Wróbel, D.; Wesołowska, A.; Duszyńska, B.; Bojarski, A. J.; Pawłowski, M. Biorg. Med. Chem. 2011, 19, 6750.
(d) Xie, L.-Y.; Peng, S.; Tan, J.-X.; Sun, R.-X.; Yu, X.; Dai, N.-N.; Tang, Z.-L.; Xu, X.; He, W.-M. ACS Sustainable Chem. Eng. 2018, 6, 16976.
[3] (a) Kong, L.; Yu, S.; Zhou, X.; Li, X. Org. Lett. 2016, 18, 588.
(b) Zheng, J.; Li, Z.; Huang, L.; Wu, W.; Li, J.; Jiang, H. Org. Lett. 2016, 18, 3514.
(c) An, X.-D.; Yu, S. Org. Lett. 2015, 17, 2692.
(d) Kong, L.; Zhou, Y.; Huang, H.; Yang, Y.; Liu, Y.; Li, Y. J. Org. Chem. 2015, 80, 1275.
(e) Xie, L.-Y.; Peng, S.; Fan, T.-G.; Liu, Y.-F.; Sun, M.; Jiang, L.-L.; Wang, X.-X.; Cao, Z.; He, W.-M. Sci. China Chem. 2019, 62, 460.
(f) Liu, B.; Gao, H.; Yu, Y.; Wu, W.; Jiang, H. J. Org. Chem. 2013, 78, 10319.
[4] (a) Zhang, Y.; Chen, W.; Jia, X.; Wang, L.; Li, P. Chem. Commun. 2019, 55, 2785.
(b) Sun, D.; Yin, K.; Zhang, R. Chem. Commun. 2018, 54, 1335.
(c) Deng, Q.; Xu, Y.; Liu, P.; Tan, L.; Sun, P. Org. Chem. Front. 2018, 5, 19.
(d) Wu, Z.-G.; Liang, X.; Zhou, J.; Yu, L.; Wang, Y.; Zheng, Y.-X.; Li, Y.-F.; Zuo, J.-L.; Pan, Y. Chem. Commun. 2017, 53, 6637.
(e) Zhang, L.; Chen, S.; Gao, Y.; Zhang, P.; Wu, Y.; Tang, G.; Zhao, Y. Org. Lett. 2016, 18, 1286.
[5] (a) Wei, Y.; Zhou, Q.-Q.; Tan, F.; Lu, L.-Q.; Xiao, W.-J. Synthesis 2019, 51, 3021.
(b) Xie, L.-Y.; Bai, Y.-S.; Xu, X.-Q.; Peng, X.; Tang, H.-S.; Huang, Y.; Lin, Y.-W.; Cao, Z.; He, W.-M. Green Chem. 2020, 22, 1720.
(c) Peng, S.; Lin, Y.-W.; He, W.-M. Chin. J. Org. Chem. 2020, 40, 541(in Chinese). (彭莎, 林英武, 何卫民, 有机化学, 2020, 40, 541.)
(d) Xie, L.-Y.; Chen, Y.-L.; Qin, L.; Wen, Y.; Xie, J.-W.; Tan, J.-X.; Huang, Y.; Cao, Z.; He, W.-M. Org. Chem. Front. 2019, 6, 3950.
[6] (a) Yang, F.-L.; Wang, F.-X.; Wang, T.-T.; Wang, Y.-J.; Tian, S.-K. Chem. Commun. 2014, 50, 2111.
(b) Bao, W.-H.; Wang, Z.; Tang, X.; Zhang, Y.-F.; Tan, J.-X.; Zhu, Q.; Cao, Z.; Lin, Y.-W.; He, W.-M. Chin. Chem. Lett. 2019, 30, 2259.
(c) Wei, W.; Liu, C.; Yang, D.; Wen, J.; You, J.; Suo, Y.; Wang, H. Chem. Commun. 2013, 49, 10239.
[7] (a) Taniguchi, T.; Idota, A.; Ishibashi, H. Org. Biomol. Chem. 2011, 9, 3151.
(b) Zhang, M.; Xie, P.; Zhao, W.; Niu, B.; Wu, W.; Bian, Z.; Pittman, C. U.; Zhou, A. J. Org. Chem. 2015, 80, 4176.
(c) Li, X.; Xu, X.; Hu, P.; Xiao, X.; Zhou, C. J. Org. Chem. 2013, 78, 7343.
(d) Wei, W.; Wen, J.; Yang, D.; Guo, M.; Wang, Y.; You, J.; Wang, H. Chem. Commun. 2015, 51, 768.
(e) Li, X.; Xu, X.; Zhou, C. Chem. Commun. 2012, 48, 12240.

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可见光促进N-苯丙炔胺与磺酰肼的环化:在无碱和催化剂下快速合成3-磺酰基喹啉衍生物

Visible-Light-Induced Cycloaddition Involving N-Propargylanilines with Arylsulfonylhydrazides: Rapid Access to 3-Sulfonated Quinoline Derivatives without Base and Catalyst

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