1076-28-4Relevant articles and documents
Development of one-pot benzylic amination reactions of azine N-oxides
Liman, Menek?e,Türkmen, Yunus Emre
, p. 1723 - 1727 (2018)
An efficient one-pot synthetic methodology has been developed for the benzylic amination reactions of methyl-substituted azine N-oxides that operate under mild conditions. The reaction was found to tolerate quinoline and isoquinoline N-oxides with electron donating and withdrawing substituents as the electrophilic reaction partners as well as a broad range of nucleophilic primary, secondary and aromatic amines, affording the benzylic amination products in up to 82% yield.
An unusual de-nitro reduction of 2-substituted-4-nitroquinolines
Zhou, Yu,Li, Jian,Liu, Hong,Zhao, Linxiang,Jiang, Hualiang
, p. 8511 - 8514 (2006)
The treatment of a variety of 2-substituted-4-nitroquinolines with Sn in the presence of concentrated hydrochloric acid in ethanol at 70 °C for 2-4 h afforded unusual de-nitro products 2-substituted-quinolines in good yields.
Baker's yeast reduction of nitroarenes in NaOH media 5. Reductive cyclization of o-nitrocinnamaldehydes
Baik, Woonphil,Kim, Dong Ik,Lee, Hyun Joo,Chung, Wook-Jin,Kim, Byeong Hyo,Lee, Seok Woo
, p. 4579 - 4580 (1997)
Reduction of 2-nitrocinnamaldehydes or 4-(2'-nitrophenyl)-3-buten-2-one by bakers' yeast has been found to be cyclized in NaOH media, resulting in the formation of quinolines via cyclized N-oxides.
Rh/O2-Catalyzed C8 Olefination of Quinoline N-Oxides with Activated and Unactivated Olefins
Sharma, Ritika,Kumar, Rakesh,Sharma, Upendra
, p. 2786 - 2797 (2019)
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.
RhIII-Catalyzed Direct C8-Arylation of Quinoline N-Oxides using Diazonaphthalen-2(1H)-ones: A Practical Approach towards 8-aza BINOL
Ghosh, Bidhan,Biswas, Aniruddha,Chakraborty, Soumen,Samanta, Rajarshi
, p. 2388 - 2392 (2018)
An efficient RhIII-catalyzed redox-neutral method for the direct C8-arylation of quinoline N-oxides using diazonaphthalen-2(1H)-one as coupling partner has been demonstrated. The developed method is simple, scalable and straightforward with a w
N2H4-H2O Enabled Umpolung Cyclization of o-Nitro Chalcones for the Construction of Quinoline N-Oxides
Zhang, Guan,Yang, Kai,Wang, Shihui,Feng, Qiang,Song, Qiuling
supporting information, p. 595 - 600 (2021/02/03)
Umpolung is a unique strategy which converts the property of an atom into the opposite one. An efficient and general method for the construction of quinoline N-oxides via umpolung of carbonyl groups was developed from ortho-nitro chalcones and hydrazine i
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.
Metal-free C8-H functionalization of quinolineN-oxides with ynamides
Hu, Weican,Zhang, Feiyang,Chen, Chen,Qi, Tianhang,Shen, Yanlong,Qian, Guoying,Rong, Zhouting
supporting information, p. 6995 - 6998 (2021/07/21)
The metal-free C8-H functionalization of quinolineN-oxides with ynamides is unveiled for the first time by the intramolecular Friedel-Crafts-type reaction of quinolyl enolonium intermediates generated from Br?nsted acid-catalyzed addition of quinolineN-ox
