Synthesis of 3-Alkylthiol Pyrazoles via Regioselective Annulation Reactions of Sulfonyl Hydrazines and Ketene Dithioacetals

  • Li Yi ,
  • Wan Jieping
Expand
  • College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022

Received date: 2020-05-10

  Revised date: 2020-06-16

  Online published: 2020-07-17

Supported by

Project supported by the National Natural Science Foundation of China (No. 21861019).

Abstract

By using sulfonyl hydrazines and ketene dithioacetals as starting materials, the regioselective annulation providing 3-alkylthiolated pyrazoles has been realized in the low cost and easily available NaHSO4 catalytst. The reactions were realized in 1,4-dioxane medium and 80 ℃ heating, whereby a seris of 3-alkylthiol pyrazoles possessing N-sulfonyl structure have been efficiently synthesized.

Cite this article

Li Yi , Wan Jieping . Synthesis of 3-Alkylthiol Pyrazoles via Regioselective Annulation Reactions of Sulfonyl Hydrazines and Ketene Dithioacetals[J]. Chinese Journal of Organic Chemistry, 2020 , 40(11) : 3889 -3894 . DOI: 10.6023/cjoc202005026

References

[1] (a) Gulia, N.; Daugulis, O. Angew. Chem., Int. Ed. 2017, 56, 3630.
(b) Lee, W.-C. C.; Shen, Y.; Gutierrez, D. A.; Li, J. J. Org. Lett. 2016, 18, 2660.
(c) Boerth, J. A.; Hummel, J. R.; Ellman, J. A. Angew. Chem., Int. Ed. 2016, 55, 12650.
[2] (a) Olguin, J.; Brooker, S. Coord. Chem. Rev. 2011, 255, 203.
(b) Bailey, W. D.; Luconi, L.; Tossin, A.; Yakhvarov, D.; Flowers, S. E.; Kaminsky, W.; Kemp, R. A.; Giambastiani, G.; Goldberg, K. I. Organometallics 2015, 34, 3998.
(c) Kuwata, S.; Ikariya, T. Chem. Commun. 2014, 50, 14290.
(d) Sinha, A. K.; Vigalok, A.; Rawat, V. Tetrahedron Lett. 2019, 60, 796.
[3] (a) Yin, P.; He, C.; Shreeve, J. M. J. Mater. Chem. A 2016, 4, 1514.
(b) Dalinger, I. L.; Kormanov, A. V.; Suponitsky, K. Y.; Muravyev, N. V.; Sheremetev, A. B. Chem.-Asian J. 2018, 13, 1165.
(c) Taydakov, I. V.; Akkuzina, A. A.; Avetisov, R. I.; Khomyakov, A. V.; Saifutyarov, R. R.; Avetissov, I. C. J. Lumin. 2016, 177, 31.
(d) Li, Y.; Chang, P.; Hu, J.; Chen, T.; Wang, B.; Wang, Y.; Wang, B. Curr. Org. Chem. 2018, 24, 1407.
[4] (a) Yang, W.; Li, Y.; Ai, Y.; Obianom, O. N.; Guo, D.; Yang, H.; Sakamuru, S.; Xia, M.; Shu, Y.; Xue, F. J. Med. Chem. 2019, 62, 11151.
(b) Ahmed, W.; Yan, X.; Hu, D.; Adnan, M.; Tang, R.-Y.; Cui, Z.-N. Bioorg. Med. Chem. 2019, 27, No. UNSP 115048.
(c) Geng, R.; Zhao, Y.; Li, Y.; Liu, X.; Wang, M. Chin. J. Org. Chem. 2019, 39, 3574(in Chinese). (耿瑞, 赵宇, 李益豪, 刘鑫磊, 王明安, 有机化学, 2019, 39, 3574.)
(d) Monteiro, M. E.; Lechuga, G.; Lara, L. S.; Souto, B. A.; Vigano, M. G.; Bourguignon, S. C.; Calvet, C. M.; Oliveira, F. O. R.; Alves, C. R.; Souza-Silva, F.; Santos, M. S.; Pereira, M. C. S. Eur. J. Med. Chem. 2019, 182, 111610.
(e) Fu. Q.; Cai, P.-P.; Cheng, L.; Zhong, L.-K.; Tan, C.-X.; Shen, Z.-H.; Han, L.; Xu, T.-M.; Liu, X.-H. Pest Manage. Sci. 2019, 76, 868.
(f) Zhong, L.; Jiang, T.; Zhang, F.; Fu, Q.; Liu, X.; Xu, T.; Ding, C.; Chen, J.; Yuan, J.; Tan, C. Chin. J. Org. Chem. 2019, 39, 2655(in Chinese). (钟良坤, 江涛, 张凡, 付庆, 刘幸海, 许天明, 丁成荣, 陈杰, 袁静, 谭成侠, 有机化学, 2019, 39, 2655.)
(g) Hassan, G. S.; Rahman, D. E. A.; Abdelmajeed, E. A.; Refaey, R. H.; Salem, M. A.; Nissan, Y. M. Eur. J. Med. Chem. 2019, 171, 332.
(h) Li, W.; Li, J.; Shen, H.; Cheng, J.; Li, Z.; Xu, X. Chin. Chem. Lett. 2018, 29, 911.
(i) Bondock, S.; Fadaly, W.; Metwally, M. A. Eur. J. Med. Chem. 2010, 45, 3692.
(j) Wang, Y.; Xu, W.; Shao, S.; Xie, Y.; Wang, J. Chin. J. Chem. 2011, 29, 2039.
[5] (a) Fustero, S.; Sánchez-Roselló, M.; Barrio, P.; Simón-Fuentes, A. Chem. Rev. 2011, 111, 6984.
(b) Janin, Y. L. Chem. Rev. 2012, 112, 3924.
(c) Maddila, S.; Jonnalagadda, S. B.; Gangu, K. K.; Maddila, S. N. Curr. Org. Chem. 2017, 14, 634.
[6] (a) Heller, S. T.; Natarajan, S. R. Org. Lett. 2006, 8, 2675.
(b) Jansa, J.; Schmidt, R.; Mamuye, A. D.; Castoldi, L.; Roller, A.; Pace, V.; Holzer, W. Beilstein J. Org. Chem. 2017, 13, 895.
(c) Zhang, J.; Shao, Y.; Wang, H.; Luo, Q.; Chen, J.; Xu, D.; Wan, X. Org. Lett. 2014, 16, 3312.
[7] (a) Guo, Y.; Wang, D.; Wei, L.; Wan, J.-P. J. Org. Chem. 2019, 84, 2984.
(b) Tian, L.; Wan, J.-P.; Sheng, S. ChemCatChem 2020, 12, 2533.
(c) Zhang, Q.; Hu, B.; Zhao, Y.; Zhao, S.; Wang, Y.; Zhang, B.; Yan, S.; Yu, F. Eur. J. Org. Chem. 2020, 1154.
[8] Pearce, A. J.; Harkins, R. P.; Reiner, B. P.; Wotal, A. C.; Dunscomb, R. J.; Tonks, I. A. J. Am. Chem. Soc. 2020, 142, 4390.
[9] (a) Fricero, P.; Bialy, L.; Brown, A. W.; Czechtizky, W.; Méndez, M.; Harrity, J. P. A. J. Org. Chem. 2017, 82, 1688.
(b) Chen, Y.; Zhu, J.; Zhao, S. Chin. J. Org. Chem. 2019, 39, 1923(in Chinese). (陈樱, 祝家楠, 赵圣印, 有机化学, 2019, 39, 1923.)
(c) Gilfillan, L.; Artschwager, R.; Harkiss, A. H.; Liskamp, R. M. J.; Sutherland, A. Org. Biomol. Chem. 2015, 13, 4514.
[10] (a) Das, P.; Gondo, S.; Tokunaga, E.; Sumii, Y.; Shibata, N. Org. Lett. 2018, 20, 558.
(b) Shao, Y.; Zheng, H.; Qian, J.; Wan, X. Org. Lett. 2018, 20, 2412.
(c) Zeng, J.-L.; Chen, Z.; Zhang, F.-G.; Ma, J.-A. Org. Lett. 2018, 20, 4562.
[11] (a) Shu, W.-M.; Zheng, K.-L.; Ma, J.-R.; Sun, H.-Y.; Wang, M.; Wu, A.-X. Org. Lett. 2015, 17, 1914.
(b) Abu, T. K.; Arindam, G.; Sidick, B. R.; Mohammad, H. M. Asian J. Org. Chem. 2013, 2, 126.
[12] (a) Neumann, J. J.; Suri, M.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 7790.
(b) Li, X.; He, L.; Chen, H.; Wu, W.; Jiang, H. J. Org. Chem. 2013, 78, 3636.
(c) Zhang, T.; Bao, W. J. Org. Chem. 2013, 78, 1317.
[13] (a) Pérez-Aguilar, M. C.; Valdés, C. Angew. Chem., Int. Ed. 2013, 52, 7219.
(b) Deng, X.; Mani, N. S. Org. Lett. 2008, 10, 1307.
(c) Kong, Y.; Tang, M.; Wang, Y. Org. Lett. 2014, 16, 576.
(d) Fang, Z.; Liu, J.; Qiao, Y. Chin. J. Org. Chem. 2018, 38, 1985(in Chinese). (房智兴, 刘巨艳, 乔艳红, 有机化学, 2018, 38, 1985.)
[14] (a) Fan, Z.-P.; Li, X.-Y.; Luo, X.-E.; Fei, X.; Sun, B.; Chen, L.-C.; Shi, Z.-F.; Sun, C.-L.; Shao, X.; Zhang, H. Adv. Funct. Mater. 2017, 27, 1702318.
(b) Zhang, D.-W.; Yang, Y.; Yao, F.; Yu, Q.-Y.; Dai, S.-J. J. Nat. Med. 2012, 66, 362.
(c) Appetcchi, G. B.; D'Annibale, A.; Santilli, C.; Genova, E.; Lombardo, L.; Navarra, M. A.; Panero, S. Electrochem. Commun. 2016, 63, 26.
(d) Yao, J.; Chen, J.; He, Z.; Sun, W.; Fang, H.; Xu, W. Med. Chem. Res. 2013, 22, 3959.
[15] (a) Deng, L.; Cao, X.; Liu, Y.; Wan, J.-P. J. Org. Chem. 2019, 84, 14179.
(b) Gao, Y.; Liu, Y.; Wan, J.-P. J. Org. Chem. 2019, 84, 2243.
(c) Zhong, S.; Liu, Y.; Cao, X.; Wan, J.-P. ChemCatChem 2017, 9, 465.
(d) Li, Y.; Wan, J.-P.; Wen, C. Tetrahedron 2017, 73, 2323.
(e) Guo, Y.; Xiang, Y.; Wei, L.; Wan, J.-P. Org. Lett. 2018, 20, 3971.
(f) Peng, S.; Song, Y.; He, J.-Y.; Tang, S.-S.; Tan, J.-X.; Cao, Z.; Lin, Y.-W.; He, W.-M. Chin. Chem. Lett. 2019, 30, 2287.
(g) Xie, L.-Y.; Fang, T.-G.; Tan, J.-X.; Zhang, B.; Cao, Z.; Yang, L.-H.; He, W.-M. Green Chem. 2019, 21, 3858.
(h) Xu, X.-M.; Chen, D.-M.; Wang, Z.-L. Chin. Chem. Lett. 2020, 31, 49.
(i) Dong, D.; Chen, W.; Chen, D.; Li, L.; Li, G.; Wang, Z.; Deng, Q.; Long, S. Chin. J. Org. Chem. 2019, 39, 3190(in Chinese). (董道青, 陈文静, 陈德茂, 李丽霞, 李光辉, 王祖利, 邓企, 龙姝, 有机化学, 2019, 39, 3190.)
(j) Wang, Y.; Liu, Y. Acta Chim. Sinica 2019, 77, 418(in Chinese). (王昱赟, 刘云云, 化学学报, 2019, 77, 418.)
(k) Liu, Y.; Xiong, J.; Wei, L. Chin. J. Org. Chem. 2017, 37, 1667(in Chinese). (刘云云, 熊进, 韦丽, 有机化学, 2017, 37, 1667.)
(l) Li, L.-X.; Dong, D.-Q.; Hao, S.-H.; Wang, Z.-L. Tetrahedron Lett. 2018, 59, 1517.
[16] (a) Huang, L.; Wu, J.; Hu, J.; Bi, Y.; Huang, D. Tetrahedron Lett. 2020, 61, 151363.
(b) Wang, M.; Shi, L.; Li, Y.; Liu, Q.; Pan, L. J. Org. Chem. 2019, 84, 9603.
(c) Deng, L.; Liu, Y. ACS Omega 2018, 3, 11890.
(d) Sorabad, G. S.; Maddani, M. R. New J. Chem. 2019, 43, 5996.
(e) Garg, P.; Singh, A. Org. Lett. 2018, 20, 1320.
(e) Fang, Z.; Liu, J.; Liu, Q.; Bi, X. Angew. Chem., Int. Ed. 2014, 53, 7209.
[17] Peruncheralathan, S.; Khan, T. A.; Ila, H.; Junjappa, H. J. Org. Chem. 2005, 70, 10030.
[18] He, J.; Man, Z.; Shi, Y.; Li, C.-Y. J. Org. Chem. 2015, 80, 4816.
[19] (a) Wan, J.-P.; Hu, D.; Bai, F.; Wei, L.; Liu, Y. RSC Adv. 2016, 6, 73132.
(b) Backes, G. L.; Jursic, B. S.; Neumann, D. M. Bioorg. Med. Chem. 2015, 23, 3397.
Outlines

/