Copper-Catalyzed Intermolecular Dehydrogenative Amidation/Amination of Quinoline N-Oxides with Lactams/Cyclamines

Abstract

C-H, N-H dehydrogenative coupling of quinoline N-oxides with lactams/cyclamines has been achieved in the presence of the Cu(OAc)2 catalyst to give good to excellent yields. This study provides a new strategy for the construction of a 2-aminoquinoline skeleton via direct functionalization of aryl C-H bonds.

Copper‐Catalyzed Deoxygenative C‐2 Amination of Quinoline N‐Oxides

“…2‐Morpholinoquinoline N ‐Oxide (3a′): Light yellow solid. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.68 (d, J = 8.6 Hz, 1 H), 7.78–7.69 (m, 3 H), 7.53–7.49 (m, 1 H), 7.06 (d, J = 9.0 Hz, 1 H), 4.00–3.98 (m, 4 H), 3.63 (s, 4 H) ppm.…”

Copper-Mediated Intermolecular C–H/C–H and C–H/N–H Couplings via Aromatic C–H Cleavage

“…24) and pyridine N-oxides (Eq. 25) were developed by Su [48] and the groups of Li [49], Wu, and Cui [50], respectively. When the biologically important sulfoximine is employed as a nitrogen source, the reaction proceeds smoothly even under ambient conditions, and the enantiopure substrate is converted into the product without affecting the enantiomeric excess (Eq.…”

Recent Advances in Catalytic Functionalization of N‐Oxide Compounds via CH Bond Activation

“…The Ullman cross-coupling, [50] Buchwald-Hartwig amination, [51] and Chan-Lam oxidative coupling [52] are very important to construct aryl C À N bonds using aryl (pseudo)halides or organometallic reagents with amines or amides. [54] This catalytic system exhibits a broad substrate scope with respect to amides/ amines. [53] In 2013, Li and co-workers developed a copper-catalyzed dehydrogenative coupling of quinoline Noxides with amides/amines for the synthesis of 2-aminoquinoline (Scheme 39).…”