Synthesis and Fungicidal Activities of 2-(Amino/acetoxy)-3- (4-methylphenyl)-thieno[3,2:5,6]pyrido[4,3-d]- pyrimidin-4(3H)-one Derivatives

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (08): 1208-1212. Previous Articles Next Articles

Full Papers

2-氨基(芳氧基)-3-对甲基苯基噻吩并[3,2:5,6]吡啶并[4,3-d]嘧啶-4(3H)- 酮的合成和生物活性

刘建超，贺红武*，陈荷莲

(华中师范大学化学学院农药与化学生物学教育部重点实验室武汉 430079)

收稿日期:2010-12-08 修回日期:2011-01-29 发布日期:2011-03-17
通讯作者: 刘建超 E-mail:liujc@mail.ccnu.edu.cn

Synthesis and Fungicidal Activities of 2-(Amino/acetoxy)-3- (4-methylphenyl)-thieno[3,2:5,6]pyrido[4,3-d]- pyrimidin-4(3H)-one Derivatives

LIU Jian-Chao, HE Hong-Wu, CHEN He-Lian

(Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079)

Received:2010-12-08 Revised:2011-01-29 Published:2011-03-17
Contact: JianChao Liu E-mail:liujc@mail.ccnu.edu.cn

A novel facile synthetic method for thienopyridine derivatives was proposed via the reaction of 2-amino-thiophenes with acetoacetic ester and tin tetrachloride under heating. A series of new 2-(amino/ acetoxy)-3-(4-methylphenyl)-thieno[3,2:5,6]pyrido[4,3-d]pyrimidin-4(3H)-one derivatives had been designed and synthesized via an aza-Wittig reaction and structually confirmed by IR, ¹H NMR, EI-MS techniques, and elemental analysis. Their biological activities were also re-searched and many of them showed fungicidal activities against Fusarium oxysporium, Rhizoctonia solani, Gibberella zeae, Dothiorella gregaria and Colletotrichum gossypii to some extent. They exhibited 31.80%～82.84% inhibition against Dothiorella gregaria at 5.0×10^－5 g/mL.

Key words: acetoacetic ester, aza-Wittig reaction, thienopyridine, pyrido[4,3-d]pyrimidine, fungicidal activity

Cite this article

LIU Jian-Chao, HE Hong-Wu, CHEN He-Lian. Synthesis and Fungicidal Activities of 2-(Amino/acetoxy)-3- (4-methylphenyl)-thieno[3,2:5,6]pyrido[4,3-d]- pyrimidin-4(3H)-one Derivatives[J]. Chin. J. Org. Chem., 2011, 31(08): 1208-1212.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[2]	Min Liu, Dongyan Yang, Yumei Xiao, Wangcang Su, Fenghai Zhao, Qin Zhaohai .. Synthesis and Bioactivities of 5-Nitroimino-[1,4-2H]-1,2,4-triazolines as Olefin-Imidacloprid Mimics [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2790-2799.
[3]	Huan Xu, Hongfei Wu, Xiaoming Zhang, Xingxing Lu, Tengda Sun, Yue Qi, Yufan Lin, Xinling Yang, Li Zhang, Yun Ling. Design, Synthesis and Bioactivity of Sulfonyl Hydrazides and Hydrazides Containing Fragment 1,2,3,4-Tetrahydroisoquinoline [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 725-733.
[4]	Changxing Sun, Fuhao Zhang, Huan Zhang, Penghui Li, Lin Jiang. Design, Synthesis, Fungicidal Activity and Molecular Docking Study of Novel 2-(1-Methyl-1H-pyrazol-4-yl)pyrimidine-4-carboxamides [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 229-235.
[5]	Lei Wang, Shujing Yu, Na Yang, Baolei Wang. Studies on the Synthesis and Biological Activities of Novel Dihydroquinazolinone-Containing Caffeine Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 299-307.
[6]	Qian Zhang, Yihao Li, Leichuan Xu, Haoyun Ma, Xiangdong Li, Ming'an Wang. Synthesis and Fungicidal Activity of Novel Butenolide Compounds Containing Oxime Ether Moiety [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2438-2448.
[7]	Changkai Wang, Tengda Sun, Xuebo Zhang, Xinling Yang, Xingxing Lu, Huan Xu, Fasheng Shi, Li Zhang, Yun Ling. Design, Synthesis and Bioactivity of Novel Fluoropyrazole Hydrazides [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1527-1536.
[8]	Weiwei Wang, Yihao Li, Xinlei Liu, Yu Zhao, Mingan Wang. Synthesis and Fungicidal Activity of Novel 3,7-Dimethylocta-2,6-dienamides and 3,7-Dimethyl-6,7-dihydroxyoct-2-enamides [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3717-3725.
[9]	Jinni Liu, Yibi Xie, Qingqing Yang, Nianyu Huang, Long Wang. Ugi Four-Component Reaction Based on the in situ Capture of Amines and Subsequent Modification Tandem Cyclization Reaction: "One-Pot" Synthesis of Six- and Seven-Membered Heterocycles [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2374-2383.
[10]	Hang Liu, Shuyun Zhang, Huan Li, Yan Zhang, Zhengming Li, Baolei Wang. Synthesis and Biological Activities of Novel 8-((3,4,4-Trifluorobut-3-en-1-yl)thio)-substituted Methylxanthines and Their Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2091-2098.
[11]	Can Jin, Xile Deng, Yong Zhou, Xiaomao Zhou. Design, Synthesis, Crystal Structure, and Fungicidal Activity of L-Carvone Derivatives Containing an Oxime Ester Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2008-2018.
[12]	Hongyan Shi, Ying Zhong, Zhigang Zhao. Synthesis of Multi-substituted 1,4-Dihydroquinoline Derivatives from Morita-Baylis-Hillman (MBH) Carbonates [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 677-687.
[13]	Wei Yu, Han Wang, Li-Jing Min, Xue-Wen Hua, Xing-Hai Liu. Synthesis and Fungicidal Activity of Novel Allyl Benzoate Compounds Containing Triazole [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 826-832.
[14]	Shuyun Zhang, Hang Liu, Lei Wang, Zhengming Li, Baolei Wang. Studies on the Synthesis, Structural Characterization and Biological Activities of Novel Caffeine Derivatives Containing Substituted-Piperazine Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4075-4082.
[15]	Tang Xianjun, Lu Xingliang, Yang Dan, Zhang Min, Xiong Yongtong, Wu Qinglai, Li Junkai. Synthesis and Fungicidal Activities of Novel Tertiary Alcohol Ergosterol Biosynthesis Inhibitors Based on Phenazine-1-carboxylic Acid [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2491-2501.

2-氨基(芳氧基)-3-对甲基苯基噻吩并[3,2:5,6]吡啶并[4,3-d]嘧啶-4(3H)- 酮的合成和生物活性

Synthesis and Fungicidal Activities of 2-(Amino/acetoxy)-3- (4-methylphenyl)-thieno[3,2:5,6]pyrido[4,3-d]- pyrimidin-4(3H)-one Derivatives

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments