325856-06-2Relevant articles and documents
Synthesis of bridged benzazocines and benzoxocines by a titanium-catalyzed double-reductive umpolung strategy
Bichovski, Plamen,Haas, Thomas M.,Kratzert, Daniel,Streuff, Jan
, p. 2339 - 2342 (2015/02/05)
A sequence of two titanium(III)-catalyzed reductive umpolung reactions is reported that allows the rapid construction of benzazo- and benzoxozine building blocks. The first step is a reductive cross-coupling of quinolones or chromones with Michael acceptors. This reaction proceeds with complete syn-selectivity for the quinolone functionalization while the anti-diastereomers are obtained as the major products from chromones. With different reaction conditions, the stereochemical outcome can be altered to afford the syn-chromanone products as well. A subsequent reductive ketyl radical cyclization forges the tricyclic title compounds in good yields. A stereochemical model explaining the observed stereoselectivities is provided and the product configurations were unambiguously verified by X-ray analyses and 2D NMR spectroscopic experiments.
Direct C-3-alkenylation of quinolones via palladium-catalyzed C-H functionalization
Li, Mingzong,Li, Liangxi,Ge, Haibo
supporting information; experimental part, p. 2445 - 2449 (2010/12/25)
An unprecedented C-3-alkenylation of quinolones was reported through palladium-catalyzed C-H functionalization with 1% catalyst loading. This method provides an efficient route to a variety of new quinolone derivatives.