TMSBr-Promoted Cascade Cyclization of <i>ortho</i>-Propynol Phenyl Azides for the Synthesis of 4-Bromo Quinolines and Its Applications

TMSBr-Promoted Cascade Cyclization of <i>ortho</i>-Propynol Phenyl Azides for the Synthesis of 4-Bromo Quinolines and Its Applications

Difficult-to-access 4-bromo quinolines are constructed directly from easily prepared <i>ortho</i>-propynol phenyl azides using TMSBr as acid-promoter. The cascade transformation performs smoothly to generate desired products in moderate to excellent yields with good functional groups com...

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Bibliographic Details
Main Authors: Fengyan Jin, Tao Yang, Xian-Rong Song, Jiang Bai, Ruchun Yang, Haixin Ding, Qiang Xiao
Format: Article
Language:English
Published: MDPI AG 2019-11-01
Series:Molecules
Subjects:
tmsbr
propargylic alcohols
azides
cascade cyclization
4-bromo quinolines
Online Access:https://www.mdpi.com/1420-3049/24/21/3999
Description
Summary:Difficult-to-access 4-bromo quinolines are constructed directly from easily prepared <i>ortho</i>-propynol phenyl azides using TMSBr as acid-promoter. The cascade transformation performs smoothly to generate desired products in moderate to excellent yields with good functional groups compatibility. Notably, TMSBr not only acted as an acid-promoter to initiate the reaction, and also as a nucleophile. In addition, 4-bromo quinolines as key intermediates could further undergo the coupling reactions or nucleophilic reactions to provide a variety of functionalized compounds with molecular diversity at C4 position of quinolines.
ISSN:1420-3049

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