Citation: Liu Jianchao, Ren Qingyun, He Hongwu. Synthesis and Herbicidal Activity of 6-Alkoxy(aryloxy) Multisubstituted Pyridine Derivatives[J]. Chinese Journal of Organic Chemistry, ;2016, 36(9): 2225-2231. doi: 10.6023/cjoc201603026 shu

Synthesis and Herbicidal Activity of 6-Alkoxy(aryloxy) Multisubstituted Pyridine Derivatives

Liu Jianchao ^a ,
Ren Qingyun ^b,*,, ,
He Hongwu ^a,*,,

a.
College of Chemistry, Central China Normal University, Wuhan, 430079
b.
Anti-infection Innovation Department, New Drug Research Institute, HEC Pharma Co., LTD, Dongguan 523871

Corresponding author: Ren Qingyun, renqingyun@hecpharm.com He Hongwu, he1208@mail.ccnu.edu.cn
Received Date: 15 March 2016
Revised Date: 15 April 2016

Fund Project: National Program on Key Basic Research Project 2010CB126100and the Natural Science Foundation of Hubei Province 2014CFA111the National Natural Science Fundation of China 31000867the Program for Changjiang Scholars and Innovatives Research Team in University IRT0953National Program on Key Basic Research Project 973 Programthe National Natural Science Fundation of China 21172090

Figures(3)

Alkyl multisubstituted pyridine-2-yl sulfones have been designed and synthesized from 6-alkylthiopyridine using H₂O₂ and NaWO₃·2H₂O as catalysts in N, N-dimethylformamide (DMF). A series of new 6-alkoxy(aryloxy) multisubstituted pyridine derivatives have been synthesized from alkyl multisubstituted pyridine-2-yl sulfone and alcohol or phenol using K₂CO₃ (NaOC₂H₅ or NaOCH₃) as catalyst in CH₃CN. The structures of target compounds have been confirmed by ¹H NMR, ¹³C NMR, EI-MS, IR spectroscopy and elemental analysis. The structure of 4-amino-5-cyano-2-methyl-6-(3-nitryl phenoxy) nicotinic acid methyl ester has been determined by single crystal X-ray diffraction. The results of preliminary bioassay indicated that some compounds possess moderate herbicidal activities against the rape and barnyard grass and show obvious selectivity.
- alkylthiopyridine,
- alkoxypyridine,
- nicotinic acid,
- NaWO₃·2H₂O,
- herbicidal activity
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