Synthesis of 3-Alkylthiol Pyrazoles via Regioselective Annulation Reactions of Sulfonyl Hydrazines and Ketene Dithioacetals
- Corresponding author: Wan Jieping, wanjieping@jxnu.edu.cn
Citation:
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
(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.
(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.
(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.
(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.
(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.
(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.
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.
doi: 10.1021/jacs.9b13173
(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.
(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.
(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.
(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.
(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.
Peruncheralathan, S.; Khan, T. A.; Ila, H.; Junjappa, H. J. Org. Chem. 2005, 70, 10030.
doi: 10.1021/jo051771u
He, J.; Man, Z.; Shi, Y.; Li, C.-Y. J. Org. Chem. 2015, 80, 4816.
doi: 10.1021/acs.joc.5b00521
(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.
Yaqin Zheng , Lian Zhuo , Meng Li , Chunying Rong . Enhancing Understanding of the Electronic Effect of Substituents on Benzene Rings Using Quantum Chemistry Calculations. University Chemistry, 2025, 40(3): 193-198. doi: 10.12461/PKU.DXHX202406119
Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
Caixia Lin , Ting Liu , Zhaojiang Shi , Hong Yan , Keyin Ye , Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107
Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
.
CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
. CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO2 by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By 1H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
Zihao Guo , Shichen Ma , Kin Shing Chan . 烯烃环化反应中6电子试剂的等瓣相似性和等电子关系. University Chemistry, 2025, 40(6): 160-166. doi: 10.12461/PKU.DXHX202408038
Nan Xiao , Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099
Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu3+ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb2+ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084