Chinese Journal of Organic Chemistry >
Synthesis and Phototoxic Activity of Isoxazole and Pyrazoline Derivatives Containing α-Terthiophene
Received date: 2013-08-06
Revised date: 2013-09-29
Online published: 2013-10-11
Supported by
Project supported by the National Natural Science Foundation of China (No. 21105030) and the Key Academic Program of 211 Project of South China Agricultural University (No. 2009B010100001).
α-Terthiophene is a class of pesticides with predominant photoactivity. In this work, using terthiophene as the lead compound, the important mediator, 2-carbonyl terthiophene, was synthesized by the carbonylation. After reaction with substituted phenylethanone, terthiophene-substituted α,β-unsaturated ketones were synthesized. Followed by the ring closure reaction with hydroxylamine hydrochloride and hydrazine, a series of 3,5-diaryl isoxazole and 3,5-diaryl pyrazoline drivatives containing α-terthiophene were synthesized, respectively. Their structures were confirmed by 1H NMR, IR and elemental analysis. The biological activity assay indicated that most of the synthesized compounds exhibit strong photoactivities. In addition, the photoactivities of isoxazole derivatives were much better than those of pyrazoline derivatives, where the photoactivity difference of compound 3b was 64.06 before and after illumination, especially. However, some of the pyrazoline derivatives showed higher activities of killing cells, where the activity of the compound 4d was as high as 83.9%.
Luo Zhigang , Liu Zhengyong , Zhang Guanglong , Ye Jiexin , Yang Zhuohong . Synthesis and Phototoxic Activity of Isoxazole and Pyrazoline Derivatives Containing α-Terthiophene[J]. Chinese Journal of Organic Chemistry, 2014 , 34(2) : 392 -397 . DOI: 10.6023/cjoc201308008
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