Facile copper-mediated activation of the N-H bond and the oxidative cleavage of the C2-C3 bond in 1H-2-phenyl-3-hydroxy-4-oxoquinoline

Miklós Czaun; Gábor Speier; László Párkányi

doi:10.1039/b315919a

Facile copper-mediated activation of the N-H bond and the oxidative cleavage of the C2-C3 bond in 1H-2-phenyl-3-hydroxy-4-oxoquinoline

Chem Commun (Camb). 2004 Apr 21:(8):1004-5. doi: 10.1039/b315919a. Epub 2004 Mar 18.

Authors

Miklós Czaun¹, Gábor Speier, László Párkányi

Affiliation

¹ Department of Organic Chemistry, University of Veszprém, 8201 Veszprém, Hungary.

PMID: 15069516
DOI: 10.1039/b315919a

Abstract

The reaction of 1H-2-phenyl-3-hydroxy-4-oxoquinoline (PhquinH(2); 1) with metallic copper leads to Cu(II)(PhquinH)(2) while in the presence of PPh(3) to Cu(I)(2)Cu(II)(Phquin)(2)(PPh(3))(4). In the presence of tmeda and O(2) ring cleavage occurs to give Cu(II)(tmeda)(PhquinH)(N-baa). Both reactions represent a mild N-H activation and an oxidative C-C bond scission.