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TMSBr-Promoted Cascade Cyclization of ortho-Propynol Phenyl Azides for the Synthesis of 4-Bromo Quinolines and Its Applications.

ABSTRACT: Difficult-to-access 4-bromo quinolines are constructed directly from easily prepared ortho-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.

SUBMITTER: Jin F 

PROVIDER: S-EPMC6864654 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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

Jin Fengyan F   Yang Tao T   Song Xian-Rong XR   Bai Jiang J   Yang Ruchun R   Ding Haixin H   Xiao Qiang Q  

Molecules (Basel, Switzerland) 20191105 21

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  ...[more]

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