Synthesis of Flavanone and Quinazolinone Derivatives from the Ruthenium-Catalyzed Deaminative Coupling Reaction of 2'-Hydroxyaryl Ketones and 2-Aminobenzamides with Simple Amines

Krishna Gnyawali; Pandula T Kirinde Arachchige; Chae S Yi

doi:10.1021/acs.orglett.1c03870

Synthesis of Flavanone and Quinazolinone Derivatives from the Ruthenium-Catalyzed Deaminative Coupling Reaction of 2'-Hydroxyaryl Ketones and 2-Aminobenzamides with Simple Amines

Org Lett. 2022 Jan 14;24(1):218-222. doi: 10.1021/acs.orglett.1c03870. Epub 2021 Dec 27.

Authors

Krishna Gnyawali¹, Pandula T Kirinde Arachchige¹, Chae S Yi¹

Affiliation

¹ Department of Chemistry, Marquette University, Milwaukee, Wisconsin 53201-1881, United States.

PMID: 34958227
DOI: 10.1021/acs.orglett.1c03870

Abstract

The cationic Ru-H complex [(C₆H₆)(PCy₃)(CO)RuH]⁺BF₄^- (1) with 3,4,5,6-tetrachloro-1,2-benzoquinone (L1) was found to be a highly effective catalyst for the deaminative coupling reaction of 2'-hydroxyaryl ketones with simple amines to form 3-substituted flavanone products. The analogous deaminative coupling reaction of 2-aminobenzamides with branched amines directly formed 3,3-disubstituted quinazolinone products. The catalytic method efficiently installs synthetically useful flavanone and quinazolinone core structures without employing any reactive reagents.

Publication types

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