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
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