Benzoquinone Ligand-Enabled Ruthenium-Catalyzed Deaminative Coupling of 2-Aminoaryl Aldehydes and Ketones with Branched Amines for Regioselective Synthesis of Quinoline Derivatives

Authors

Krishna Prasad Gnyawali, Marquette University
Aldiyar Shakenov, Marquette University
Pandula T. Kirinde Arachchige, Marquette University
Chae S. Yi, Marquette UniversityFollow

Document Type

Article

Publication Date

2024

Publisher

American Chemical Society

Source Publication

Journal of Organic Chemistry

Source ISSN

0022-3263

Original Item ID

DOI: 10.1021/acs.joc.4c00063

Abstract

The catalytic system generated in situ from the cationic Ru–H complex [(C₆H₆)(PCy₃)(CO)RuH]⁺BF₄– (1) with 2,3,4,5-tetrachloro-1,2-benzoquinone (L1) was found to be highly effective for promoting the deaminative coupling reaction of 2-aminoaryl aldehydes with branched amines to form 2-substituted quinoline products. The analogous deaminative coupling reaction of 2-aminoaryl ketones with branched amines led to the regioselective formation of 2,4-disubstituted quinoline products. A number of biologically active quinoline derivatives including graveolinine and a triplex DNA intercalator have been synthesized by using the catalytic method.

Comments

Accepted version. Journal of Organic Chemistry, Vol. 89, No. 16 (2024): 11119-11135. DOI. © 2024 American Chemical Society. Used with permission.

Recommended Citation

Gnyawali, Krishna Prasad; Shakenov, Aldiyar; Arachchige, Pandula T. Kirinde; and Yi, Chae S., "Benzoquinone Ligand-Enabled Ruthenium-Catalyzed Deaminative Coupling of 2-Aminoaryl Aldehydes and Ketones with Branched Amines for Regioselective Synthesis of Quinoline Derivatives" (2024). Chemistry Faculty Research and Publications. 1094.
https://epublications.marquette.edu/chem_fac/1094