Synthesis of 1-Benzyl-3-(α-hydroxy-(un)substitutedbenzylidene)-pyrrolidine-2,4-diones and Biological Activity

Chin. J. Org. Chem. ›› 2005, Vol. 25 ›› Issue (04): 419-423. Previous Articles Next Articles

Original Articles

1-苄基-3-[α-羟基-(未)取代苄基叶立德]吡咯啉- 2,4-二酮的合成与生物活性

朱有全，胡方中，邹小毛，姚昌盛
刘斌，李永红，杨华铮*

(南开大学元素有机化学研究所元素有机化学国家重点实验室天津 300071)

收稿日期:2004-05-10 修回日期:2004-11-02 发布日期:2005-03-30
通讯作者: 杨华铮

Synthesis of 1-Benzyl-3-(α-hydroxy-(un)substitutedbenzylidene)-pyrrolidine-2,4-diones and Biological Activity

ZHU You-Quan,HU Fang-Zhong,ZOU Xiao-Mao,YAO Chang-Sheng
LI Yong-Hong,LIU Bing,YANG Hua-Zheng*

(Institute of Elemento-Organic Chemistry, State Key Laboratory and Institute of Elemento-Organic Chemis-try,
Nankai University, Tianjin 300071)

Received:2004-05-10 Revised:2004-11-02 Published:2005-03-30
Contact: YANG Hua-Zheng

Abstract

A series of 1-benzyl-3-[α-hydroxy-(un)substitutedbenzylidene]pyrrolidine-2,4-diones were prepared in an attempt to find new kinds of herbicides. All of them have been confirmed by ¹H NMR, IR spectra and elemental analysis. The preliminary bioassay results indicated that some of them had some extent herbicidal activity against broad leaf grasses and their structure-activity relationship was discussed

Key words: p-hydroxyphenypyruvate dioxydenase, pyrrolidine, herbicide

Cite this article

ZHU You-Quan,HU Fang-Zhong,ZOU Xiao-Mao,YAO Chang-Sheng
LI Yong-Hong,LIU Bing,YANG Hua-Zheng*. Synthesis of 1-Benzyl-3-(α-hydroxy-(un)substitutedbenzylidene)-pyrrolidine-2,4-diones and Biological Activity[J]. Chin. J. Org. Chem., 2005, 25(04): 419-423.

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1-苄基-3-[α-羟基-(未)取代苄基叶立德]吡咯啉- 2,4-二酮的合成与生物活性

Synthesis of 1-Benzyl-3-(α-hydroxy-(un)substitutedbenzylidene)-pyrrolidine-2,4-diones and Biological Activity

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[1]	Lei Kang, Li Pan, Zhou Xiaoyun, Wang Shiben, Wang Xuekun, Ji Lusha, Liu Renmin, Xu Xiaohua. Design, Synthesis and Herbicidal Activity of 5-Acylbarbituric Acid Derivatives and Study of Molecular Mode of Action [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2788-2797.
[2]	Yang Sen, Ding Chengrong, Liu Xinghai, Weng Jianquan, Yuan Jing, Tan Chengxia. Synthesis and Herbicidal Activity of Chiral Aryloxyphenoxypropionic Amides Compounds [J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3588-3593.
[3]	Zhang Jingang, Wu Zhengxing, Xie Fang, Zhang Wanbin. Metal-Catalyzed Unsaturated Hydrocarbon Functionalization Applied in the Synthesis of Pyrrolidines and Pyrrolines [J]. Chin. J. Org. Chem., 2018, 38(6): 1319-1326.
[4]	He Bo, Wang Dawei, Yang Wenchao, Chen Qiong, Yang Guangfu. Advances in Research on 4-Hydroxyphenylpyruvate Dioxygenase (HPPD) Structure and Pyrazole-Containing Herbicides [J]. Chin. J. Org. Chem., 2017, 37(11): 2895-2904.
[5]	Zhang Xiaoxiang, Sun Xiaoping, Rao Weidong. Triflic Acid-Catalyzed Tandem Reactions of Cyclopropyl Alcohols with Sulfonamides for the Synthesis of Pyrrolidines [J]. Chin. J. Org. Chem., 2015, 35(7): 1500-1505.
[6]	Yuan Dongpeng, Zeng Ming, Bai Chunmei, Cui Dongmei, Zhang Chen. Synthesis of N-Sulfonyl Pyrrolidines Catalyzed by IPrAuCl/AgOTf [J]. Chin. J. Org. Chem., 2014, 34(6): 1231-1234.
[7]	Dai Lingling, Cui Shengfeng, Damu Guri L. V., Zhou Chenghe. Recent Advances in the Synthesis and Application of Tetrazoles [J]. Chin. J. Org. Chem., 2013, 33(02): 224-244.
[8]	. Synthesis and Herbicidal Activities of 2-(o-4,6-Dimethoxylpyrimidinyl- 2-oxo(thio)phenyl-1,3,4-thia(oxa)diazoles [J]. Chin. J. Org. Chem., 2011, 31(08): 1202-1207.
[9]	DONG Xiao-Liang, ZHOU Yu-Han, XU Shan-Shan, QU Jing-Ping. Synthesis and Herbicidal Activity of 5-Arylmethoxy Phenylpyrazole Derivatives [J]. Chin. J. Org. Chem., 2011, 31(07): 1020-1026.
[10]	SI Teng-Fei, MENG Fan-Gui, WANG Xian-Feng, ZHU Zhao-Yong, QIANG Sheng, YANG Chun-Long. Synthesis and Herbicidal Activities of (Z,E)-1-[1-(2,4-Dioxo- pyrrolidine-3-ylidene)ethyl]-4-alkylsemicarbazide Derivatives [J]. Chin. J. Org. Chem., 2011, 31(04): 521-527.
[11]	HU De-Jin, LIU Su-Fang, HUANG Tong-Hui, TU Hai-Yang, LI Wei-Guo, ZHU Xiao-Lei, ZHANG Ai-Dong. Synthesis and Herbicidal Activities of N^ε-Anilinocarbonyl-N^α-{3-[(un)- substituted phenyl]isoxazol-5-ylcarbonyl}lysine Derivatives [J]. Chin. J. Org. Chem., 2010, 30(9): 1366-1371.
[12]	WANG Tao, LUO Jin, ZHENG Cai-Hua. Synthesis and Herbicidal Activity of 3,6-Dialkylthio-1- phenyl-pyrazolo[3,4-d]pyrimidin-4-ones [J]. Chin. J. Org. Chem., 2010, 30(11): 1749-1753.
[13]	ZHU You-Quan, ZHU Ran, YUAN Yan-Wei, ZHANG Jin, WANG Wen-Hu, ZOU Xiao-Mao, HU Fang-Zhong, LIU Xiang-Ming, YANG Hua-Zheng. Synthesis and Bioactivities of Novel 3-[α-Hydroxy(indol-3-yl)- methylene]-pyrrolidine-2,4-dione Derivatives [J]. Chin. J. Org. Chem., 2010, 30(08): 1207-1211.
[14]	Xiao, Ling ; Zeng, Heping*. Synthesis, Electrochemical and Two-Photon Absorption Properties of N-Methyl-2-{N-ethyl-6-[2-(8-methoxylquinol-2-yl)vinyl]carbazol-3-yl}- fulleropyrrolidine [J]. Chin. J. Org. Chem., 2009, 29(05): 742-747.
[15]	PANG Huai-Lin,b,YANG Hai^a, YIN Du-Lin*^,a,LEI Man-Xiang^b HUANG Ming-Zhi^b,MAO Chun-Hui^b,LI Wen-An^a. Synthesis and Biological Activity of N-Alkyl-6-(3-chloro-4-chloromethyl-2-oxopyrrolidin-1-yl)-7-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-one Derivatives [J]. Chin. J. Org. Chem., 2007, 27(9): 1130-1136.