6563-13-9Relevant articles and documents
Energetics of 6-methoxyquinoline and 6-methoxyquinoline N-oxide: The dissociation enthalpy of the (N-O) bond
Da Silva, Maria D.M.C. Ribeiro,Santos, Luis M.N.B.F.,Silva, Ana L.R.,Fernandes, Oscar,Acree Jr.
, p. 1093 - 1100 (2003)
The standard (p° = 0.1MPa) molar enthalpies of formation, at T = 298.15K, were determined using static-bomb calorimetry for crystalline 6-methoxyquinoline N-oxide (6MeOQUINO), as -(85.6 ± 3.7) kJ·mol-1 and liquid 6-methoxyquinoline (6MeOQUI), -(25.8 ± 2.2)kJ·mol-1. The standard molar enthalpies of sublimation/vaporization, at T = 298.15K, were measured by microcalorimetry and from the enthalpies of formation of the gaseous compounds, the dissociation enthalpy Dm0 of the (N+-O-) dative covalent bond was derived, as (269.2 ± 5.0)kJ·mol-1.
Quinoline Ligands Improve the Classic Direct C?H Functionalisation/Intramolecular Cyclisation of Diaryl Ethers to Dibenzofurans
Mackey, Katrina,Jones, David J.,Pardo, Leticia M.,McGlacken, Gerard P.
supporting information, p. 495 - 498 (2021/01/12)
The C?H functionalisation approach to the synthesis of dibenzofurans is hampered by a number of problems. Herein we describe the evolution of a cheap, bench stable quinoline ligand, which obviates most of the current limitations and allows for a high yielding synthesis of a range of valuable dibenzofurans. Dibenzofurans are important motifs in natural products and compounds with wide biological activity.
Deoxygenative C2-heteroarylation of quinoline N-oxides: Facile access to α-Triazolylquinolines
Sontakke, Geetanjali S.,Shukla, Rahul K.,Volla, Chandra M. R.
supporting information, p. 485 - 493 (2021/03/22)
A metal-and additive-free, highly efficient, step-economical deoxygenative C2-heteroarylation of quinolines and isoquinolines was achieved from readily available N-oxides and N-sulfonyl-1,2,3-Triazoles. A variety of α-Triazolylquinoline derivatives were synthesized with good regioselectivity and in excellent yields under mild reaction conditions. Further, a gram-scale and one-pot synthesis illustrated the efficacy and simplicity of the developed protocol. The current transformation was also found to be compatible for the late-stage modification of natural products.
