Study on the Chlorination Reaction of Hydrazones by Using of Trichloroisocyanuric Acid as Chloride Source
- Corresponding author: Hu Yulai, huyl@nwnu.edu.cn
Citation:
Zong Wuzhong, Hu Yulai, Wang Xiaoping, Liu Jiaxin, Huang Danfeng, Wang Kehu. Study on the Chlorination Reaction of Hydrazones by Using of Trichloroisocyanuric Acid as Chloride Source[J]. Chinese Journal of Organic Chemistry,
;2019, 39(5): 1396-1403.
doi:
10.6023/cjoc201811039
For selected recent artiles see:
(a) Sharma, P.; Bhat, S. V.; Prabhath, M. R. R; Molino, A.; Nauha, E.; Wilson, D. J. D.; Moses, J. E. Org. Lett. 2018, 20, 4263.
(b) Guo, C.-X.; Zhang, W.-Z.; Zhang, N.; Lu, X.-B. J. Org. Chem. 2017, 82, 7637.
(c) Liu, H.; Jia, H.; Wang, B.; Xiao, Y.; Guo, H. Org. Lett. 2017, 19, 4714.
(d) Tsai, S.-E.; Yen, W.-P.; Li, Y.-T.; Hu, Y.-T.; Tseng, C.-C.; Wong, F. F. Asian J. Org. Chem. 2017, 6, 1470.
(e) Wang, G.; Liu, X.; Huang, T.; Kuang, Y.; Lin, L.; Feng, X. Org. Lett. 2013, 15, 76.
(f) Fuchi, N.; Doi, T.; Takahashi, T. Chem. Lett. 2005, 34, 438.
(a) Zhao, H.-W.; Zhao, Y.-D.; Liu, Y.-Y.; Zhao, L.-J.; Song, X.-Q.; Chen, X.-Q.; Pang, H.-L.; Du, J.; Feng, N.-N. RSC Adv. 2017, 7, 55106.
(b) Garve, L. K. B.; Petzold, M.; Jones, P. G.; Werz, D. B. Org. Lett. 2016, 18, 564.
Guo, Z.; Jia, H.; Liu, H.; Wang, Q.; Huang, J.; Guo, H. Org. Lett. 2018, 20, 2939.
doi: 10.1021/acs.orglett.8b00990
Ulrich, H. The Chemistry of Imidoyl Halides, Plenum Press, New York, 1968; Chapter 7, p. 173.
Patel, H. V.; Vyas, K. A.; Pandey, S. P.; Fernandes, P. S. Tetrahedron 1996, 52, 661.
doi: 10.1016/0040-4020(95)00916-7
(a) Pinto, G.; Rohrig, B. J. Chem. Educ. 2003, 80, 41.
(b) Tilstam, U.; Weinmann, H. Org. Process Res. Dev. 2002, 6, 384.
(a) Gaspa, S.; Porcheddu, A.; Luca, L. D. Adv. Synth. Catal. 2016, 358, 154.
(b) Gaspa, S.; Porcheddu, A.; Luca, L. D. Org. Lett. 2015, 17, 3666.
(c) Jing, Y.; Daniliuc, C. G.; Studer, A. Org. Lett. 2014, 16, 4932.
Tanaka, K.; Maeno, S.; Mitsuhashi, K. J. Heterocycl. Chem. 1985, 22, 565.
doi: 10.1002/jhet.v22:2
Corey, E. J.; Kim, C. U. J. Am. Chem. Soc. 1972, 94, 7586.
doi: 10.1021/ja00776a056
Yatham, V. R.; Harnying, W.; Kootz, D.; Neudorfl, J.-M.; Schlorer, N. E.; Berkessel, A. J. Am. Chem. Soc. 2016, 138, 2670.
doi: 10.1021/jacs.5b11796
Wojciechowska, A.; Jasinski, M.; Kaszynski, P. Tetrahedron 2015, 71, 2349.
doi: 10.1016/j.tet.2015.03.015
Giustiniano, M.; Meneghetti, F.; Mercalli, V.; Varese, M.; Giustiniano, F.; Novellino, E.; Tron, G. C. Org. Lett. 2014, 16, 5332.
doi: 10.1021/ol502515b
Palazzino, G.; Cecchi, H.; Melani, F.; Colotta, V.; Filacchioni, G.; Martini, C.; Lucacchini, A. J. Med. Chem. 1987, 30, 1737.
doi: 10.1021/jm00393a009
Ellsworth, B. A.; Shi, J.; Ewing, W. R.; Jurica, E. A.; Hernandez, A. S.; Wu, X. US 0142139, 2014[Chem. Abstr. 2014, 161, 830876].
Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au23(S-Adm)16 and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
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
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
Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050
Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
Jingjie Tang , Luying Xie , Jiayu Liu , Shangyu Shi , Xinyu Sun , Jiayang Lin , Qikun Yang , Chuan'ang Yu , Zecheng Wang , Yingying Wang , Zengyang Xie . Efficient Rapid Synthesis and Antibacterial Activities of Tosylhydrazones: A Recommended Innovative Chemistry Experiment for Undergraduate Medical University. University Chemistry, 2024, 39(3): 316-326. doi: 10.3866/PKU.DXHX202309091
Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065