Citation: 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]. Chinese Journal of Organic Chemistry, ;2018, 38(7): 1680-1686. doi: 10.6023/cjoc201801016 shu

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

Corresponding author: Ma Wei, mawei@hljucm.net Wang Daolin, wangdaolin@sina.com
Received Date: 8 January 2018
Revised Date: 25 March 2018
Available Online: 12 July 2018
Fund Project: the Harbin Research and Development Fund of Applied Technology 2017RAQXJ129the National Public Welfare Industry Special 201404718the Scientific Research Fund of the Health Planning Committee of Heilongjiang 2017-579the National Natural Science Foundation of China 31770688Project 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)

Figures(2)

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