Organometal-Free Arylation and Arylation/Trifluoroacetylation of Quinolines by Their Reaction with CF3-ynones and Base-Induced Rearrangement

Vasiliy M Muzalevskiy; Kseniya V Belyaeva; Boris A Trofimov; Valentine G Nenajdenko

doi:10.1021/acs.joc.0c01277

Organometal-Free Arylation and Arylation/Trifluoroacetylation of Quinolines by Their Reaction with CF₃-ynones and Base-Induced Rearrangement

J Org Chem. 2020 Aug 7;85(15):9993-10006. doi: 10.1021/acs.joc.0c01277. Epub 2020 Jul 20.

Authors

Vasiliy M Muzalevskiy¹, Kseniya V Belyaeva², Boris A Trofimov², Valentine G Nenajdenko¹

Affiliations

¹ Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991 Russia.
² A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Street, Irkutsk 664033, Russia.

PMID: 32631065
DOI: 10.1021/acs.joc.0c01277

Abstract

The reaction of quinolines with CF₃-ynones resulted in the formation of 1,3-oxazinoquinolines. Subsequent treatment of the reaction mixture with a base initiated deep structural transformation of primary products. Both steps proceed in very high yield. As a result, unusual rearrangement of 1,3-oxazinoquinolines to form either 2-arylquinolines or 2-aryl-3-trifluoroacetylquinolines was discovered. The decisive role of the base in the reaction direction was shown. Using these reactions, highly efficient pathways to 2-arylquinolines and 2-aryl-3-trifluoroacetylquinolines were elaborated to provide the corresponding compounds in high yields using a simple one-pot procedure. The possible mechanism of rearrangement is discussed.

Publication types

Research Support, Non-U.S. Gov't