Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 16, Pages 2735-2740Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700495
Keywords
benzo[d]isoxazoles; [4+2] cascade annulation; Lewis acid catalysis; propargylic alcohols; quinoline derivatives
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Funding
- National Science Foundation [NSF 21472073, 21532001]
- National Science Foundation of Jiangxi Province [20161BAB213085]
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An unprecedented copper(II) trifluoromethanesulfonate-catalyzed [4+2] cascade annulation of propargylic alcohols with benzo[d] isoxazoles proceeds through a sequential ring opening/Meyer-Schuster rearrangement/intermolecular cyclization. This protocol, which tolerates a broad variety of functional groups, offers a versatile, modular and atom-economical access to a new class of fascinating quinoline derivatives in good yields under mild conditions. The transformation could be scaled up to a gram scale efficiently, thus highlighting the synthetic utility of this methodology.
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