17104-69-7Relevant articles and documents
Deoxygenative Amination of Azine-N-oxides with Acyl Azides via [3 + 2] Cycloaddition
Ghosh, Prithwish,Han, Sang Hoon,Han, Sangil,Kim, Dongeun,Kim, In Su,Kim, Saegun,Kwon, Na Yeon,Mishra, Neeraj Kumar
, p. 2476 - 2485 (2020/03/13)
A transition-metal-free deoxygenative C-H amination reaction of azine-N-oxides with acyl azides is described. The initial formation of an isocyanate from the starting acyl azide via a Curtius rearrangement can trigger a [3 + 2] dipolar cycloaddition of polar N-oxide fragments to generate the aminated azine derivative. The applicability of this method is highlighted by the late-stage and sequential amination reactions of complex bioactive compounds, including quinidine and fasudil. Moreover, the direct transformation of aminated azines into various bioactive N-heterocycles illustrates the significance of this newly developed protocol.
Rh/O2-Catalyzed C8 Olefination of Quinoline N-Oxides with Activated and Unactivated Olefins
Sharma, Ritika,Kumar, Rakesh,Sharma, Upendra
, p. 2786 - 2797 (2019/02/26)
The rhodium/O2 system-catalyzed distal C(sp2)-H olefination of quinoline N-oxides is developed. Molecular oxygen has been explored as an economic and clean oxidant, an alternative to inorganic oxidants. A wide substrate scope with respect to quinoline N-oxides and olefins (activated acrylates and styrenes; unactivated aliphatic olefins) demonstrates the robustness of the developed catalytic method. Interestingly, 2-substituted quinoline N-oxides also afforded good yields of the corresponding C8-olefinated products. Kinetic isotope studies and deuterium-labeling experiments have been performed to understand the preliminary mechanistic pathway. The applicability of the developed method is demonstrated by utilizing natural product-derived substrates and by converting the C8-olefinated quinoline N-oxides into various other useful molecules.
2-Position-Selective Trifluoromethylthiolation of Six-Membered Heteroaromatic Compounds
Muta, Ryuhei,Torigoe, Takeru,Kuninobu, Yoichiro
supporting information, (2019/06/13)
The regioselective C-H trifluoromethylthiolation of six-membered heteroaromatic compounds via nucleophilic attack of a CF3S source on the electrophilically activated six-membered heteroaromatic ring was developed. The reaction proceeds in good yield with good functional group tolerance, even on a gram-scale. The key to the successful regioselective transformation is the presence of an additive (2,4-dinitrobenzenesulfonyl chloride). The regioselective trifluoromethylthiolation of quinidine derivative is also demonstrated. Trifluoromethylthiolation, followed by S-oxidation, affords the corresponding sulfones.
