Citation: ZONG Guang-Ning, LI Feng-Yun, FAN Zhi-Jin, MAO Wu-Tao, SONG Hai-Bin, CHEN Lai, ZHU Yu-Jie, XU Jing-Hua, SONG Yin-Qi, WANG Jia-Ran. Synthesis, Crystal Structure and Biological Activity of 2-(3,4-Dichloroisothiazol-5-yl)-4-(trifluoromethyl)-4,5-dihydrothiazol-4-yl-3-methylbenzoate[J]. Chinese Journal of Structural Chemistry, ;2015, 34(6): 871-878. doi: 10.14102/j.cnki.0254-5861.2011-0598 shu

Synthesis, Crystal Structure and Biological Activity of 2-(3,4-Dichloroisothiazol-5-yl)-4-(trifluoromethyl)-4,5-dihydrothiazol-4-yl-3-methylbenzoate

1.
a State Key Laboratory of Elemento-organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, China;
2.
b College of Chemistry and Pharmacy Engineering, Nanyang Normal University, Nanyang, Henan 473061, China

Received Date: 8 December 2014
Available Online: 31 March 2015
Fund Project: This study was funded in part by the Tianjin Natural Science Foundation (No.14JCYBJC20400) (No.14JCYBJC20400) the "111" Project of Ministry of Education of China (No.B06005) (No.B06005)NFFTBS (No.J1103306) (No.J1103306)

The title compound diethyl 2-(3,4-dichloroisothiazol-5-yl)-4-(trifluoromethyl)-4,5-dihydrothiazol-4-yl-3-methylbenzoate (C₁₅H₉C_l2F₃N₂O₂S₂, M_r=441.26) was prepared from methyl 3,4-dichloroisothiazole-5-carboxylate as the starting material by four steps of reaction. Its structure was characterized by IR, 1H-NMR, ¹³C-NMR, EA and single-crystal X-ray diffraction. The crystal of the title compound belongs to the monoclinic system, space group P2₁/c with a=8.8437(18), b=16.128(3), c=12.305(3) Å, β=91.68(3)°, V=1754.4(6) Å³, Z=4, D_c=1.671 g/cm³, μ(MoKa)=0.71073 mm^-1, F(000)=888, R=0.0384 and wR=0.0778. Weak π-π interactions occur between the isothiazole rings and phenyl rings of adjacent molecules to form a one-dimensional chain and stabilize the crystal structure. Bioassay indicates that the title compound has good activity against the fungi and TMV tested.
- isothiazole,
- 4,5-dihydrothiazole,
- synthesis,
- crystal structure,
- biological activity
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