Citation: LI Juan-Juan, HUA Xue-Wen, FAN Zhi-Jin, JI Xiao-Tian, ZONG Guang-Ning, LI Feng-Yun, HUANG Yun, SONG Hai-Bin, LIU Chao-Lun, Yury Yu. Morzherin, Nataliy P. Belskaya, Vasiliy A. Bakulev. Synthesis, Crystal Structure and Biological Activity of Diethyl 1,4-dihydro-2,6-dimethyl-4-(4-methyl-1,2,3-thiadi azol-5-yl)pyridine-3,5-dicarboxylate[J]. Chinese Journal of Structural Chemistry, ;2014, 33(4): 535-543. shu

Synthesis, Crystal Structure and Biological Activity of Diethyl 1,4-dihydro-2,6-dimethyl-4-(4-methyl-1,2,3-thiadi azol-5-yl)pyridine-3,5-dicarboxylate

a.
a. Department of Plant Pathology, Sichuan Agricultural University, Chengdu 611130, China;
b.
b. State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China;
c.
c. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China;
d.
d. The Ural Federal University Named after the First President of Russia B. N. Yeltsin, Yeltsin UrFU 620002, Ekaterinburg, Russia

Corresponding author: FAN Zhi-Jin,
Received Date: 12 September 2013
Available Online: 24 December 2013
Fund Project:

The title compound diethyl 1,4-dihydro-2,6-dimethyl-4-(4-methyl-1,2,3-thiadiazol-5-yl) pyridine-3,5-dicarboxylate (C₁₆H₂₁N₃O₄S, M_r=351.42) was prepared by the Hantszch reaction with 4-methyl-1,2,3-thiadiazole-5-formaldehyde, ethyl acetoacetate and ammonium acetate in the presence of aluminum chloride in alcohol, and its structure was characterized by IR spectra, ¹H-NMR, EA, and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic system, space group P2₁/n with a=11.300(2), b=12.771(3), c=12.826(3) Å, β=96.55(3)°, V=1839.0(6) Å³, Z=4, D_c=1.296 g/cm³, μ(MoKa)=0.71073 mm^-1, F(000)=744, R=0.0981 and wR=0.1994. X-ray diffraction result shows that the torsion angles of N(1)-C(2)-C(3)-C(4) and C(2)-C(3)-C(4)-C(8) are 178.9(3)° and -130.3(3)°, respectively. All rings in the title compound are non-planar. The bioassay results indicate that the title compound has good fungicidal activity, good antivirus activity against tobacco mosaic virus and certain extent of insecticidal activity against Mythimna separata.
- 1,4-dihydropyridine,
- 1,2,3-thiadiazole,
- crystal structure,
- biological activity
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