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ChemInform Abstract: Quinoline Synthesis: Scope and Regiochemistry of Photocyclization of Substituted Benzylidenecyclopentanone O-Alkyl and O-Acetyloximes.

✍ Scribed by Mark Austin; Oliver J. Egan; Raymond Tully; Albert C. Pratt

Publisher
John Wiley and Sons
Year
2008
Weight
48 KB
Volume
39
Category
Article
ISSN
0931-7597

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✦ Synopsis

Fused pyridine derivatives R 0450

Quinoline Synthesis: Scope and Regiochemistry of Photocyclization of Substituted Benzylidenecyclopentanone O-Alkyl and O-Acetyloximes. -The study of various oximes reveals that the nature of the leaving group does not affect the cyclization. The reactions of meta-substituted precursors are highly regioselective: alkyl substituents lead to 5-substituted products (XIV), whereas more strongly electron-donating substituents give 7-substituted derivatives. Substrates (Ic), (Id), and (XXIV) (cf. following scheme) do not react. Oximes bearing Ο€-systems other than the benzylidene phenyl group also produce fused quinolines (to be continued). -(AUSTIN, M.; EGAN, O.

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