Synthesis and molluscicidal activity of new cinnoline and pyrano [2,3-c]pyrazole derivatives
Synthesis and molluscicidal activity of new cinnoline and pyrano [2,3-c]pyrazole derivatives
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DOI：
10.1002/ardp.200600057
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发表时间：
2006-08-01
影响因子：
5.1
通讯作者：
El-Mahrouky, Sherif F.
中科院分区：
文献类型：
--
作者：
Abdelrazek, Fathy M.;Metz, Peter;El-Mahrouky, Sherif F.
2-（3-羟基-5，5-二甲基亚环己基）丙二腈5与芳基重氮盐进行偶氮偶联反应，得到3-氨基-2-芳基-6，6-二甲基-8-氧代-2，6，7，8-四氢噌啉4-腈7。在乙酸中回流后，将这些化合物乙酰化，得到噌啉衍生物9。吡唑酮10 a、B与3-糠叉基-和3-噻吩叉基-丙二腈衍生物11 a、B反应，得到吡喃并[2，3-c]吡唑衍生物13 a-d。这些新合成的化合物对亚历山大双脐螺（Biomphalaria alexandrina）有一定的杀螺活性。
2-(3-Hydroxy-5,5-dimethylcyclohexylidene)malononitrile 5 undergoes an azo coupling reaction with aryldiazonium salts to afford 3-amino-2-aryl-6,6-dimethyl-8-oxo-2,6,7,8-tetrahydrocinnoline4-carbonitriles 7. Upon reflux in acetic acid, these compounds were acetylated to give the cinnoline derivatives 9. The pyrazolones 10a, b react with 3-furfurylidene- and 3-thienylidene-malononitrile derivatives 11a, b to afford the pyrano[2,3-c]pyrazole derivatives 13a - d. These newly synthesized compounds show generally a moderate molluscicidal activity to Biomphalaria alexandrina snails.