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Synthesis and Molluscicidal Activity of New Cinnoline and Pyrano [2,3‐ c ]pyrazole Derivatives
Author(s) -
Abdelrazek Fathy M.,
Metz Peter,
Metwally Nadia H.,
ElMahrouky Sherif F.
Publication year - 2006
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200600057
Subject(s) - malononitrile , pyrazolones , cinnoline , chemistry , pyrazole , acetic acid , pyrazolone , aryl , medicinal chemistry , organic chemistry , stereochemistry , catalysis , alkyl
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‐tetrahydrocinnoline‐4‐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.