1613-37-2Relevant articles and documents
Conformational and structural analysis of bis(4-chloroquinoline-N-oxide)hydrogen tribromide
Romanov,Nizhnik, Ya. P.,Fofanov
, p. 365 - 369 (2015)
The X-ray diffraction and conformational study of bis(4-chloroquinoline-N-oxide)hydrogen tribromide is performed. Two conformations corresponding to the minima on the energy curve are found by DFT using the ABINIT software. The model of one of the conformers generally matches with the structure determined experimentally for this compound using X-ray diffraction. In both instances, the structure with the dihedral angle (quinoline - N-O-H) close to 90° is most favorable, which is explained in terms of resonance theory and steric factors. It is concluded that oxygen atoms in the complex are in the sp3 hybridization state and the sp2 hybrid state of the oxygen atom is not possible here due to steric factors.
13C NMR studies on the structure of 5H- and 6H-indolo-[2,3-b] quinolines and the related compounds
Kamieńska-Trela,Kania,Bechcicka,Kaczmarek
, p. 209 - 218 (2003)
A set of 13C NMR data which included one-bond spin-spin coupling constants has been obtained for a large series of heteroaromatic compounds. It contains, among others, 6-substituted quinolines, their N-oxides, 2- and 5-methoxyindoles. The results obtained for these basic molecules were compared with those measured for a series of variously substituted 5H- and 6H-indolo[2,3-b]quinolines, which shed new light on the electronic structure of the two latter groups of the compounds.
Heterogeneous mesoporous manganese oxide catalyst for aerobic and additive-free oxidative aromatization of N-heterocycles
Mullick, Kankana,Biswas, Sourav,Angeles-Boza, Alfredo M.,Suib, Steven L.
, p. 2256 - 2259 (2017)
Herein, we report a heterogeneous, aerobic, additive-free and environmentally benign catalytic protocol for oxidative aromatization of saturated nitrogen-heterocycles using a mesoporous manganese oxide material. The aromatized products can be separated by easy filtration and the catalyst is reusable for at least four cycles. Mechanistic investigation provides evidence for radical intermediates, a multi-electron redox cycle between Mn centers, and an oxygen exchange mechanism.
Copper-Catalyzed Deoxygenative C2-Sulfonylation of Quinoline N -Oxides with DABSO and Phenyldiazonium Tetrafluoroborates for the Synthesis of 2-Sulfonylquinolines via a Radical Reaction
Deng, Qi,Dong, Dao-Qing,Li, Guang-Hui,Wang, Zu-Li,Yan, Shi-Qiang
, p. 3313 - 3319 (2019)
An efficient and practical method for the synthesis of 2-sulfonylquinolines through copper-catalyzed deoxygenative C2-sulfonylation of quinoline N -oxides with 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) and phenyldiazonium tetrafluoroborates is demonstrated. Products with various substituents were obtained in moderate to high yields.
A photochemical C=C cleavage process: Toward access to backbone N-formyl peptides
Ball, Zachary T.,Wang, Haopei
supporting information, p. 2932 - 2938 (2022/01/12)
Photo-responsive modifications and photo-uncaging concepts are useful for spatiotemporal control of peptides structure and function. While side chain photo-responsive modifications are relatively common, access to photo-responsive modifications of backbone N-H bonds is quite limited. This letter describes a new photocleavage pathway, affording N-formyl amides from vinylogous nitroaryl precursors under physiologically relevant conditions via a formal oxidative C=C cleavage. The N-formyl amide products have unique properties and reactivity, but are difficult or impossible to access by traditional synthetic approaches.
SO2F2-mediated oxidation of primary and tertiary amines with 30% aqueous H2O2 solution
Liao, Xudong,Zhou, Yi,Ai, Chengmei,Ye, Cuijiao,Chen, Guanghui,Yan, Zhaohua,Lin, Sen
supporting information, (2021/11/01)
A highly efficient and selective oxidation of primary and tertiary amines employing SO2F2/H2O2/base system was described. Anilines were converted to the corresponding azoxybenzenes, while primary benzylamines were transformed into nitriles and secondary benzylamines were rearranged to amides. For tertiary amine substrates quinolines, isoquinolines and pyridines, their oxidation products were the corresponding N-oxides. The reaction conditions are very mild and just involve SO2F2, amines, 30% aqueous H2O2 solution, and inorganic base at room temperature. One unique advantage is that this oxidation system is just composed of inexpensive inorganic compounds without the use of any metal and organic compounds.
