Study on the Chlorination Reaction of Hydrazones by Using of Trichloroisocyanuric Acid as Chloride Source

doi:10.6023/cjoc201811039

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (5): 1396-1403.DOI: 10.6023/cjoc201811039 Previous Articles Next Articles

Articles

三氯异氰尿酸促进下腙的氯化反应研究

宗吴中, 胡雨来, 王小平, 刘佳欣, 黄丹凤, 王克虎

西北师范大学化学化工学院兰州 730070

收稿日期:2018-11-30 修回日期:2019-01-17 发布日期:2019-01-31
通讯作者: 胡雨来 E-mail:huyl@nwnu.edu.cn
基金资助:
国家自然科学基金（No.21662030）资助项目.

Study on the Chlorination Reaction of Hydrazones by Using of Trichloroisocyanuric Acid as Chloride Source

Zong Wuzhong, Hu Yulai, Wang Xiaoping, Liu Jiaxin, Huang Danfeng, Wang Kehu

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received:2018-11-30 Revised:2019-01-17 Published:2019-01-31
Contact: 10.6023/cjoc201811039 E-mail:huyl@nwnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21662030).

1. Study on the Chlorination Reaction of Hydrazones by Using of Trichloroisocyanuric Acid as Chloride Source.PDF(13178KB)

Abstract

The chlorination reaction of hydrazones with N-aryltrifluoroacetohydrazones by using trichloroisocyanuric acid as chlorine source was investigated, and a series of N-arylhydrazonyl chlorides and N-aryltrifluoroacetohydrazonyl chlorides were obtained in high yields. This method had advatages of easy operation, short reaction time, mild conditions and the use of stable and cheap chlorine source, which provides an efficiant method for the synthesis of N-arylhydrazonyl chlorides and N-aryltrifluoroacetohydrazonyl chlorides.

Key words: trichloroisocyanuric acid, chlorination reaction, hydrazonyl chlorides, trifluoroacetohydrazonyl chlorides, synthesis

Cite this article

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]. Chin. J. Org. Chem., 2019, 39(5): 1396-1403.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Singh, M. S.; Chowdhury, S.; Koley, S. Tetrahedron 2016, 72, 1603.
(b) Hashimoto, T.; Maruoka, K. Chem. Rev. 2015, 115, 5366.
(c) Shawali, A. S. Chem. Rev. 1993, 93, 2731.
(d) Hu, X.; Liu, B.; Liu, H.; Li, X. Chin. J. Org. Chem. 2013, 33, 1583(in Chinese). (胡小莲, 刘彬, 刘浩冲, 李筱芳, 有机化学, 2013, 33, 1583.)
[2] 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.
[3] (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.
[4] Guo, Z.; Jia, H.; Liu, H.; Wang, Q.; Huang, J.; Guo, H. Org. Lett. 2018, 20, 2939.
[5] Ulrich, H. The Chemistry of Imidoyl Halides, Plenum Press, New York, 1968; Chapter 7, p. 173.
[6] Patel, H. V.; Vyas, K. A.; Pandey, S. P.; Fernandes, P. S. Tetrahedron 1996, 52, 661.
[7] (a) Pinto, G.; Rohrig, B. J. Chem. Educ. 2003, 80, 41.
(b) Tilstam, U.; Weinmann, H. Org. Process Res. Dev. 2002, 6, 384.
[8] (a) Su, Y.; Shi, Y.; Chang, B.; Wu, L.; Chong, S.; Zhang, W.; Huang, D.; Wang, K.-H.; Hu, Y. Chin. J. Org. Chem. 2018, 38, 1454(in Chinese). (苏瀛鹏, 石娅, 常兵兵, 吴丽丽, 种思颖, 张为钢, 黄丹凤, 王克虎, 胡雨来, 有机化学, 2018, 38, 1454.)
(b) Motati, D. R.; Uredi, D.; Watkins, E. B. Chem. Sci. 2018, 9, 1782.
(c) Combe, S. H.; Hosseini, A.; Parra, A.; Schreiner, P. R. J. Org. Chem. 2017, 82, 2407.
(d) Zhao, N.; Xuan, S.; Fronczek, F. R.; Smith, K. M.; Vicente, M. G. H. J. Org. Chem. 2015, 80, 8377.
(e) D'Oyley, J. M.; Aliev, A. E.; Sheppard, T. D. Angew. Chem. Int. Ed. 2014, 53, 10747.
(f) Vo, T. T.; Zhang, J.; Parrish, D. A.; Twamley, B.; Shreeve, J. M. J. Am. Chem. Soc. 2013, 135, 11787.
[9] (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.
[10] Tanaka, K.; Maeno, S.; Mitsuhashi, K. J. Heterocycl. Chem. 1985, 22, 565.
[11] Corey, E. J.; Kim, C. U. J. Am. Chem. Soc. 1972, 94, 7586.
[12] Yatham, V. R.; Harnying, W.; Kootz, D.; Neudorfl, J.-M.; Schlorer, N. E.; Berkessel, A. J. Am. Chem. Soc. 2016, 138, 2670.
[13] Wojciechowska, A.; Jasinski, M.; Kaszynski, P. Tetrahedron 2015, 71, 2349.
[14] Giustiniano, M.; Meneghetti, F.; Mercalli, V.; Varese, M.; Giustiniano, F.; Novellino, E.; Tron, G. C. Org. Lett. 2014, 16, 5332.
[15] Palazzino, G.; Cecchi, H.; Melani, F.; Colotta, V.; Filacchioni, G.; Martini, C.; Lucacchini, A. J. Med. Chem. 1987, 30, 1737.
[16] Ellsworth, B. A.; Shi, J.; Ewing, W. R.; Jurica, E. A.; Hernandez, A. S.; Wu, X. US 0142139, 2014[Chem. Abstr. 2014, 161, 830876].

三氯异氰尿酸促进下腙的氯化反应研究

Study on the Chlorination Reaction of Hydrazones by Using of Trichloroisocyanuric Acid as Chloride Source

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[2]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[3]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[4]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[7]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[8]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[9]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[10]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[11]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[12]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[13]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[14]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[15]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.