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某些1,3,4-三芳基-5-氯吡唑、吡喃并[2,3-c]吡唑、吡唑基酞嗪和吡喃并[2,3-d]噻唑衍生物的合成及其杀螺活性

Synthesis and molluscicidal activity of some 1,3,4-triaryl-5-chloropyrazole, pyrano[2,3-c]pyrazole, pyrazolylphthalazine and pyrano[2,3-d]thiazole derivatives.

作者信息

Abdelrazek Fathy M, Michael Farid A, Mohamed Alaa E

机构信息

Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt.

出版信息

Arch Pharm (Weinheim). 2006 Jun;339(6):305-12. doi: 10.1002/ardp.200500259.

Abstract

2-(5-Chloro-1,3-diphenyl-1H-pyrazol-4-ylmethylene)-malononitrile 1a reacts with the arylidenes of malononitrile 2a-d to afford the triaryl-5-chloropyrazoles 3a-d, respectively. 1a reacts with the active methylene pyrazolinones 5a, b and 12a, b to afford different products 8, 9, 10, 11, and 14a, b--depending on the substitution in the pyrazole ring. Compound 1a reacts also with the pyridazinone derivative 15 to afford the phthalazinone 16, and with the thiazolinones 17a-c to afford the pyrano[2,3-d]thiazoles 20a-c, respectively. It reacts also with the malononitrile dimer 21a and with ethyl cyanoacetate dimer 21b to yield the pyrazolyl pyridines 22a, b, respectively. The synthesized compounds showed a moderate molluscicidal activity towards Biomphalaria alexandrina snails.

摘要

2-(5-氯-1,3-二苯基-1H-吡唑-4-基亚甲基)-丙二腈1a与丙二腈2a-d的亚芳基反应,分别得到三芳基-5-氯吡唑3a-d。1a与活性亚甲基吡唑啉酮5a、b和12a、b反应,根据吡唑环上的取代情况得到不同的产物8、9、10、11以及14a、b。化合物1a还与哒嗪酮衍生物15反应得到酞嗪酮16,与噻唑啉酮17a-c反应分别得到吡喃并[2,3-d]噻唑20a-c。它还与丙二腈二聚体21a以及氰基乙酸乙酯二聚体21b反应,分别生成吡唑基吡啶22a、b。合成的化合物对埃及钉螺显示出中等程度的杀螺活性。

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