15936-11-5Relevant academic research and scientific papers
Visible-Light-Mediated Aerobic Oxidation of N-Alkylpyridinium Salts under Organic Photocatalysis
Jin, Yunhe,Ou, Lunyu,Yang, Haijun,Fu, Hua
supporting information, p. 14237 - 14243 (2017/10/17)
Quinolones and isoquinolones exhibit diverse biological and pharmaceutical activities, and their synthesis is highly desirable under mild conditions. Here, a highly efficient and environmentally friendly visible light-mediated aerobic oxidation of readily available N-alkylpyridinium salts has been developed with Eosin Y as the organic photocatalyst and air as the terminal oxidant, and the reaction provided quinolones and isoquinolones in good yields. The method shows numerous advantages including mild and environmentally friendly conditions, high efficiency, tolerance of wide functional groups and low cost. Furthermore, 4-desoxylonimide with important pharmaceutical activities was effectively prepared by using our method. Therefore, the present method should provide a novel and useful strategy for synthesis and modification of N-heterocycles.
Imination of N-Methylazinium Salts by Liquid Ammonia/Potassium Permanganate
Wozniak, M.,Buurman, D.J.,Plas, H.C. van der
, p. 765 - 769 (2007/10/02)
Treatment of 1-methylquinolinium-, 1,4-dimethylquinolinium- and 1-methyl-1,X-naphthyridinium iodides (X=5,8) with liquid ammonia/potassium permanganate leads to introduction of the imino group at C-2 forming the 1,2-dihydro-2-imino-1-methylquinolines and 1,2-dihydro-2-imino-1-methyl-1,X-naphthyridines (X=5,8) respectively. 1,2-Dimethylquinolinium iodide, when subjected to treatment with liquid ammonia/potassium permanganate undergoes an oxo-demethylation reaction, yielding 1-methylquinol-2-one.The nmr-measurements of solutions of the above-mentioned salts in liquid ammonia clearly show the formation of ?-adduct, strongly suggesting that these ?-adducts are intermediates in the imination reactions.
