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Base‐Catalyzed Cascade Reaction of ortho ‐(Propargylamino)aryl Ketones with N‐, O‐, or S‐Based Nucleophiles for the Synthesis of 3‐Functionalized Quinoline Scaffolds
Author(s) -
Yu LiuZhu,
Wei HaoZhao,
Shi Min
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800120
Subject(s) - chemistry , quinoline , aryl , catalysis , nucleophile , combinatorial chemistry , base (topology) , cascade reaction , organic chemistry , primary (astronomy) , cascade , mathematical analysis , alkyl , physics , mathematics , astronomy , chromatography
Abstract A metal‐free and base‐catalyzed cascade reaction of ortho ‐(propargylamino)aryl ketones with primary alcohols, secondary amines, including various N‐heterocycles, and thiols through 1,4‐benzoxazepine intermediates was developed, providing a series of synthetically and medically valuable 3‐functionalized quinoline derivatives. The reaction process was easily manipulable and environmentally benign, producing 1.0 equiv. of water as the sole byproduct. Furthermore, bimolecular reactions for the synthesis of products containing two quinoline units were also succesful by utilizing this newly developed protocol.