Lossen rearrangement by Rh(III)-catalyzed C-H activation/annulation of aryl hydroxamates with alkynes: access to quinolone-containing amino acid derivatives

Dmitry A Petropavlovskikh; Daria V Vorobyeva; Ivan A Godovikov; Sergey E Nefedov; Oleg A Filippov; Sergey N Osipov

doi:10.1039/d1ob01711j

Lossen rearrangement by Rh(III)-catalyzed C-H activation/annulation of aryl hydroxamates with alkynes: access to quinolone-containing amino acid derivatives

Org Biomol Chem. 2021 Nov 10;19(43):9421-9426. doi: 10.1039/d1ob01711j.

Authors

Dmitry A Petropavlovskikh¹, Daria V Vorobyeva¹, Ivan A Godovikov¹, Sergey E Nefedov², Oleg A Filippov¹, Sergey N Osipov¹

Affiliations

¹ A.N. Nesmeyanov Institute of Organoelement compounds, Russian Academy of Sciences, Vavilov str. 28, 119991 Moscow, Russia. osipov@ineos.ac.ru.
² N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky pr. 31, 119991, Moscow, Russia.

PMID: 34668894
DOI: 10.1039/d1ob01711j

Abstract

A convenient and robust method for the preparation of new CF₃-containing 2-quinolones has been developed via a Rh(III)-catalyzed C-H activation/Lossen rearrangement/annulation cascade of N-pivaloyloxy-arylamides with internal alkynes bearing an α-CF₃-α-amino acid moiety on the triple bond. This work expands the scope of valuable products that are available through C-H activation/annulation reactions of arylamides in organic synthesis.

Publication types

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