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

Abstract

Fused pyridine derivatives R 0450Quinoline 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 π-systems other than the benzylidene phenyl group also produce fused quinolines (to be continued). -(AUSTIN, M.; EGAN, O. J.; TULLY, R.; PRATT*, A. C.; Org. Biomol. Chem. 5 (2007) 23, 3778-3786; Sch. Chem. Sci., Dublin City Univ., Dublin 9, Ire.; Eng.) -Klein 15-148