Chinese Journal of Organic Chemistry >
Synthesis and Herbicidal Activity of 6-Alkoxy(aryloxy) Multisubstituted Pyridine Derivatives
Received date: 2016-03-15
Revised date: 2016-04-15
Online published: 2016-05-17
Supported by
Project supported by the National Program on Key Basic Research Project (973 Program, No.2010CB126100), the National Natural Science Fundation of China (Nos.21172090, 31000867), the Program for Changjiang Scholars and Innovatives Research Team in University (No.IRT0953) and the Natural Science Foundation of Hubei Province (No.2014CFA111).
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.
Key words： alkylthiopyridine; alkoxypyridine; nicotinic acid; NaWO3·; 2H2O; herbicidal activity
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
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