Stereoselective Synthesis and Biological Properties of (αE,E)-α-Me- th-oxymino-2-[(1-arylalkylidene)aminooxymethyl]-benzeneacetates

Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (01): 110-115. Previous Articles Next Articles

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(αE,E)-α-(甲氧亚氨基)-2-[1-(芳香醛酮肟氧基)甲基]苯乙酸甲酯的立体选择性合成及生物活性研究

李焰*^,1,2，张洪权¹，周叶兵¹，刘杰¹，陈祖兴¹，刘钊杰²

(¹湖北大学化学与材料科学学院武汉 430062)
(²华中师范大学国家教育部农药化学重点实验室武汉 430079)

收稿日期:2005-03-24 修回日期:2005-07-12 发布日期:2005-12-31
通讯作者: 李焰

Stereoselective Synthesis and Biological Properties of (αE,E)-α-Me- th-oxymino-2-[(1-arylalkylidene)aminooxymethyl]-benzeneacetates

LI Yan*^,1,2,ZHANG Hong-Quan¹,ZHOU Ye-Bing¹,LIU Jie¹
CHEN Zu-Xin¹,LIU Zhao-Jie²

(¹ Faculty of Chemistry and Material Science, Hubei University, Wuhan 430062)
(² Key Laboratory of Pesticide and Chemical Biology of the Ministry of Education of China,
Central China Normal University, Wuhan 430079)

Received:2005-03-24 Revised:2005-07-12 Published:2005-12-31
Contact: LI Yan

Abstract

In this paper, E-toluene-2-α-hydroxyiminoacetate was stereoselectively obtained by the coupling reaction of toluene-2-diazonium chloride with methyl glyoxylate oxime ester in the presence of CuSO₄/Na₂SO₃, and then methylated with dimethyl sulfate using sodium hydride as base to yield the key intermediate methyl E-2-methoxyimino-2-o-tolylacetate. The intermediate was brominated by NBS and then eth-erified with E-aryloxime to afford (αE,E)-α-methoxyimino-2-[(1-arylalkylidene)aminooxymethyl]-benze- neacetates. Most of the compounds all possess high activities against a wide variety of fungi.

Key words: fungicide, stereoselective coupling reaction, strobilurin, E-2-methoxyimino-2-o-tolylacetate

Cite this article

LI Yan*^,1,2,ZHANG Hong-Quan,ZHOU Ye-Bing,LIU Jie
CHEN Zu-Xin,LIU Zhao-Jie². Stereoselective Synthesis and Biological Properties of (αE,E)-α-Me- th-oxymino-2-[(1-arylalkylidene)aminooxymethyl]-benzeneacetates[J]. Chin. J. Org. Chem., 2006, 26(01): 110-115.

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(αE,E)-α-(甲氧亚氨基)-2-[1-(芳香醛酮肟氧基)甲基]苯乙酸甲酯的立体选择性合成及生物活性研究

Stereoselective Synthesis and Biological Properties of (αE,E)-α-Me- th-oxymino-2-[(1-arylalkylidene)aminooxymethyl]-benzeneacetates

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