Chinese Journal of Organic Chemistry >
Synthesis and Fungicidal Activity of Novel Benzothiophene-Fused Pyrido[1,2-a]pyrimidine Derivatives
Received date: 2018-01-08
Revised date: 2018-03-25
Online published: 2018-04-12
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).
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.
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
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