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.
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http://dx.doi.org/10.1021/ol402324v | DOI Listing |
Org Lett
December 2024
Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, P.O. Box 173, Lucknow 226031, India.
A Lewis acid-mediated C2-trifluoroethylamidation of quinolines, employing quinoline oxides, trifluorodiazoethane, and acetonitrile to forge a new class of (quinolin2-yl)-(trifluoroethyl)acetamide is presented in this Letter. The reaction proceeds through a carbene generation/nitrile ylide formation/(3 + 2) cycloaddition/rearrangement cascade to furnish quinoline-2-(trifluoroethyl)acetamide derivatives in high yields.
View Article and Find Full Text PDFOrg Lett
December 2024
School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
The synthesis of (iso)quinoline-indole hybrids by reacting (iso)quinoline -oxides with -alkynylanilines in the presence of a combination of copper(II) catalyst and a bidentate 2,2'-bipyridine ligand is described. The utility of this method was demonstrated through site-selective functionalization of the synthesized products. A plausible reaction pathway for site-selective amination followed by annulative indole formation was elucidated by a series of mechanistic investigations.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
October 2024
Department of Chemistry, University of Illinois Chicago 845 West Taylor Street, Chicago, 60607, Illinois, USA.
Electrochemical reduction of 2-allyl-substituted nitroarenes using a simple, undivided electrochemical cell with non-precious electrodes to generate nitroarene radical anions was developed. The nitroarene radical anion intermediates participate in 1,5-hydrogen atom transfer reactions to construct quinoline N-oxides bearing aryl-, heteroaryl-, alkenyl-, benzyl-, sulfonyl-, or carboxyl groups.
View Article and Find Full Text PDFAdv Sci (Weinh)
December 2024
State Key Laboratory of Organometallic Chemistry and Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS, 345 Lingling Road, Shanghai, 200032, P. R. China.
The transition metal-catalyzed direct coupling reactions involving electron-rich Fischer carbene species are largely underdeveloped and remain a big challenge. Here, a direct coupling reaction of azoles and azine N-oxides is reported with Fischer copper carbene species bearing an α-siloxy group i, which can be in situ generated from acylsilanes catalytically under photoirradiation and redox-neutral conditions. This coupling reaction between electron-rich α-siloxy Fischer Cu-carbene species with hard carbanion nucleophiles may undergo a bimetallic relay process, which is confirmed by the kinetic analysis and in situ NMR analysis.
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October 2024
Laboratory of New Energy & New Functional Materials, Shaanxi Key Laboratory of Chemical Reaction Engineering, College of Chemistry and Chemical Engineering, Yan'an University, Yan'an 716000, P. R. China.
A Cu(I)-catalyzed highly regioselective synthesis of 2-acetamidequinoline -oxides using dioxazolones with quinoline -oxides has been reported. The reaction possesses mild reaction conditions and excellent functional group compatibility. Furthermore, the addition of hydrochloric acid promotes the decomposition of copper complexes, which is beneficial for postprocessing.
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