Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Selectfluor-Triggered Tandem Cyclization of o-Hydroxyarylenaminones To Access Difluorinated 2-Amino-Substituted Chromanones

Selectfluor-Triggered Tandem Cyclization of o-Hydroxyarylenaminones To Access Difluorinated 2-Amino-Substituted Chromanones
Hua Yang, Peng-Ju Xia, Qinglan Zhao, Jun-Jie Wang, Jun-An Xiao, Xiaoqing Chen, Haoyue Xiang
A practical and straightforward synthetic route through a Selectfluor-triggered tandem cyclization of o-hydroxyarylenaminone was developed to construct a variety of difluorinated 2-amino-substituted chromanones. This novel protocol features mild reaction conditions, operational simplicity, and broad substrate scope. The enamine moiety in o-hydroxyarylenaminone played dual roles to enable high efficiency in the difluorination and intramolecular cyclization, leading to the accomplishment of a new class of difluorinated 2-amino-substituted chromanones for pharmaceutical studies.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01339

DOI: 10.1021/acs.joc.7b01339

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