Citation: CHEN Wei, WANG Hao-An, WEI Wei, LI Yu-Xin, HUA Xue-Wen, SONG Hai-Bin, YU Shu-Jing, LI Zheng-Ming. Regioselective Synthesis, Crystal Structure and Biological Activity of Novel 2-Phenylsulfonylhydrazono-3-(3-trifluoromethylphenyl)-2(3H)-thiazoline Derivatives[J]. Chinese Journal of Structural Chemistry, ;2015, 34(4): 503-509. doi: 10.14102/j.cnki.0254-5861.2011-0563 shu

Regioselective Synthesis, Crystal Structure and Biological Activity of Novel 2-Phenylsulfonylhydrazono-3-(3-trifluoromethylphenyl)-2(3H)-thiazoline Derivatives

a.
a. State Key Laboratory of Elemento-organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Nankai University, Tianjin 300071, China;
b.
b. Tianjin Nankai High School, Tianjin 300100, China

Received Date: 6 November 2014
Available Online: 8 January 2015
Fund Project: This project was supported by the National Natural Science Foundation of China (No. 21272129) (No. 21272129)the National Key Technologies R&D Program (2011BAE06B05) (2011BAE06B05)

The title compounds 2-phenylsulfonylhydrazono-3-(3-trifluoromethylphenyl)-2(3H)-thiazoline derivatives were designed and synthesized via the reaction of thiosemicarbazides with chloroacetaldehyde, and their chemical structures were characterized by ¹H NMR, ¹³C NMR, elemental analysis and MS. Furthermore, 4a was characterized by single-crystal X-ray diffraction. The target compound 4a (C₁₆H₁₂F₃N₃O₂S₂, M_r=399.41) crystallized in monoclinic system, P2₁/c space group with a=7.7457(4), b=13.5850(7), c=16.5455(10)Å, β=99.698(2)°, V=1656.30(16)Å³, D_c=1.602 g/cm³, Z=4, F(000)=816, λ=0.71070Å, μ(MoKα)=0.370 mm^-1, R=0.072 and wR=0.0867. The crystal structure of 4a revealed the cyclization of thiosemicarbazide moiety with chloroacetaldehyde at the N(1) position. The title compounds exhibited good insecticidal activity against spider mite (Tetranychus cinnabarinus Boisduval) and favorable fungicidal activity against Corynespora cassiicola.
- 2(3H)-thiazoline,
- regioselective cyclization,
- insecticidal activity,
- fungicidal activity
1. [1]
  Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
2. [2]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
3. [3]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
4. [4]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
5. [5]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
6. [6]
  Simin Wei , Yaqing Yang , Junjie Li , Jialin Wang , Jinlu Tang , Ningning Wang , Zhaohui Li . The Mn/Yb/Er triple-doped CeO₂ nanozyme with enhanced oxidase-like activity for highly sensitive ratiometric detection of nitrite. Chinese Chemical Letters, 2024, 35(6): 109114-. doi: 10.1016/j.cclet.2023.109114
7. [7]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
8. [8]
  Ruiying Liu , Li Zhao , Baishan Liu , Jiayuan Yu , Yujie Wang , Wanqiang Yu , Di Xin , Chaoqiong Fang , Xuchuan Jiang , Riming Hu , Hong Liu , Weijia Zhou . Modulating pollutant adsorption and peroxymonosulfate activation sites on Co3O4@N,O doped-carbon shell for boosting catalytic degradation activity. Chinese Journal of Structural Chemistry, 2024, 43(8): 100332-100332. doi: 10.1016/j.cjsc.2023.100332
9. [9]
  Maosen Xu , Pengfei Zhu , Qinghong Cai , Meichun Bu , Chenghua Zhang , Hong Wu , Youzhou He , Min Fu , Siqi Li , Xingyan Liu . In-situ fabrication of TiO₂/NH₂−MIL-125(Ti) via MOF-driven strategy to promote efficient interfacial effects for enhancing photocatalytic NO removal activity. Chinese Chemical Letters, 2024, 35(10): 109524-. doi: 10.1016/j.cclet.2024.109524
10. [10]
  Xinyi Hu , Riguang Zhang , Zhao Jiang . Depositing the PtNi nanoparticles on niobium oxide to enhance the activity and CO-tolerance for alkaline methanol electrooxidation. Chinese Journal of Structural Chemistry, 2023, 42(11): 100157-100157. doi: 10.1016/j.cjsc.2023.100157
11. [11]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
12. [12]
  Guo-Ping Yin , Ya-Juan Li , Li Zhang , Ling-Gao Zeng , Xue-Mei Liu , Chang-Hua Hu . Citrinsorbicillin A, a novel homotrimeric sorbicillinoid isolated by LC-MS-guided with cytotoxic activity from the fungus Trichoderma citrinoviride HT-9. Chinese Chemical Letters, 2024, 35(8): 109035-. doi: 10.1016/j.cclet.2023.109035
13. [13]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
14. [14]
  Yiyue Ding , Qiuxiang Zhang , Lei Zhang , Qilu Yao , Gang Feng , Zhang-Hui Lu . Exceptional activity of amino-modified rGO-immobilized PdAu nanoclusters for visible light-promoted dehydrogenation of formic acid. Chinese Chemical Letters, 2024, 35(7): 109593-. doi: 10.1016/j.cclet.2024.109593
15. [15]
  Qi Tan , Run-Zhu Fan , Wencong Yang , Ge Zou , Tao Chen , Jianying Wu , Bo Wang , Sheng Yin , Zhigang She . (+)/(−)-Mycosphatide A, a pair of highly oxidized polyketides with lipid-lowering activity from the mangrove endophytic fungus Mycosphaerella sp. SYSU-DZG01. Chinese Chemical Letters, 2024, 35(9): 109390-. doi: 10.1016/j.cclet.2023.109390
16. [16]
  Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836
17. [17]
  Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
18. [18]
  Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
19. [19]
  Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp³)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
20. [20]
  Baohua LÜ , Yuzhen LI . Anisotropic photoresponse of two-dimensional layered α-In₂Se₃(2H) ferroelectric materials. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1911-1918. doi: 10.11862/CJIC.20240105

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(590)
HTML views(19)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return