Synthesis and Fungicidal Activity of Novel Benzothiophene-Fused Pyrido[1,2-a]pyrimidine Derivatives

doi:10.6023/cjoc201801016

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (7): 1680-1686.DOI: 10.6023/cjoc201801016 Previous Articles Next Articles

Articles

新型苯并噻吩稠合吡啶并[1,2-a]嘧啶衍生物的合成及其抑菌活性

徐姣^a,b, 马玲^a, 刘秀波^b, 马伟^a,b, 马岩^c, 王道林^d

a 东北林业大学林木遗传育种国家重点实验室哈尔滨 150040;
b 黑龙江中医药大学药学院哈尔滨 150040;
c 哈尔滨商业大学工商管理学院哈尔滨 150040;
d 渤海大学化学化工学院锦州 121003

收稿日期:2018-01-08 修回日期:2018-03-25 发布日期:2018-04-12
通讯作者: 马伟, 王道林 E-mail:mawei@hljucm.net;wangdaolin@sina.com
基金资助:
国家自然科学基金（No.31770688）、国家公益性行业专项（No.201404718）、哈尔滨市应用技术研究与开发资金（No.2017RAQXJ129）和黑龙江省卫生计生委科研基金（No.2017-579）资助项目.

Synthesis and Fungicidal Activity of Novel Benzothiophene-Fused Pyrido[1,2-a]pyrimidine Derivatives

Xu Jiao^a,b, Ma Ling^a, Liu Xiubo^b, Ma Wei^a,b, Ma Yan^c, Wang Daolin^d

a State Key Laboratory of Tree Genetics and Breeding, Northeast Forestry University, Harbin 150040;
b College of Pharmacy, Heilongjiang University of Chinese Medicine, Harbin 150040;
c School of business administration, Harbin University of Commerce, Harbin 150040;
d College of Chemistry and Chemical Engineering, Bohai University, Jinzhou 121003

Received:2018-01-08 Revised:2018-03-25 Published:2018-04-12
Contact: 10.6023/cjoc201801016 E-mail:mawei@hljucm.net;wangdaolin@sina.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 31770688), the National Public Welfare Industry Special (No. 201404718), the Harbin Research and Development Fund of Applied Technology (No. 2017RAQXJ129) and the Scientific Research Fund of the Health Planning Committee of Heilongjiang (No. 2017-579).

1. Synthesis and Fungicidal Activity of Novel Benzothiophene-Fused Pyrido[1,2-a]pyrimidine Derivatives.PDF(1852KB)

Abstract

A series of novel benzothieno[3',2':2,3]pyrido[4,5-d]pyrido[1,2-a]pyrimidines are prepared via Pictet-Spengler reaction of 2-(3-aminobenzothiophene-2-yl)-4H-pyrido[1,2-a]pyrimidin-4-one using sulfamic acid as a catalyst, which in turn were obtained from the Thorpe-Ziegler isomerization of 2-(chloromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one with 2-mercapto-benzonitrile. The structures of the products were characterized by FT-IR, ¹H NMR, ¹³C NMR spectra and elemental analysis. The fungicidal activities of the prepared compounds were also preliminarily evaluated. For example, 5b exhibited more than 96% inhibition rate to Botrytis cinerea and Gibberella zeae at 50 mg/L, 5f exhibited 98% inhibition rate to Sclerotonia sclerotiorum at 50 mg/L, and 5g, 5i exhibited more than 93% inhibition rate to Alternaria alternata at 50 mg/L.

Key words: pyrido[1,2-a]pyrimidine, benzothiophene, 2-mercaptobenzonitrile, Pictet-Spengler reaction, synthesis, fungicidal activity

Cite this article

Xu Jiao, Ma Ling, Liu Xiubo, Ma Wei, Ma Yan, Wang Daolin. Synthesis and Fungicidal Activity of Novel Benzothiophene-Fused Pyrido[1,2-a]pyrimidine Derivatives[J]. Chin. J. Org. Chem., 2018, 38(7): 1680-1686.

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新型苯并噻吩稠合吡啶并[1,2-a]嘧啶衍生物的合成及其抑菌活性

Synthesis and Fungicidal Activity of Novel Benzothiophene-Fused Pyrido[1,2-a]pyrimidine Derivatives

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