94708-08-4Relevant academic research and scientific papers
Quinoline synthesis: Scope and regiochemistry of photocyclisation of substituted benzylidenecyclopentanone O-alkyl and O-acetyloximes
Austin, Mark,Egan, Oliver J.,Tully, Raymond,Pratt, Albert C.
, p. 3778 - 3786 (2008/10/09)
Irradiation of substituted 2-benzylidenecyclopentanone O-alkyl and O-acetyloximes in methanol provides a convenient synthesis of alkyl, alkoxy, hydroxy, acetoxy, amino, dimethylamino and benzo substituted annulated quinolines. para-Substituents yield 6-substituted-2,3-dihydro-1H-cyclopenta[b] quinolines with 8-substituted products being obtained from ortho-substituted starting materials. Reactions of meta-substituted precursors are highly regioselective, with alkyl substituents leading to 5-substituted 2,3-dihydro-1H-cyclopenta[b]quinolines and more strongly electron-donating substituents generally resulting in 7-substituted products. 2-Furylmethylene and 2-thienylmethylene analogues yield annulated furo- and thieno-[2,3e]pyridines respectively. Sequential E- to Z-benzylidene group isomerisation and six π-electron cyclisation steps result in formation of a short-lived dihydroquinoline intermediate which spontaneously aromatises by elimination of an alcohol or acetic acid. For 2-benzylidenecyclopentanone O-allyloxime, singlet excited states are involved in both steps. The Royal Society of Chemistry 2007.
Synthesis of New Arylidencycloalkylpyrazoles of Potential Biological Interest
Cardia, M. C.,Maccioni, E.,Bonsignore, L.
, p. 310 - 316 (2007/10/03)
Indazoles and pyrazoles are known to be pharmaceutically relevant molecules. In particular their application as both analgesic and antitumoral drugs has been reported. In order to investigate the properties of compounds belonging to these families, we have synthesised new cycloalkylpyrazoles bearing an arylidene group on the cycloalkyl ring, with the aim of modifying the biological profile of these molecules.
