13221-70-0Relevant academic research and scientific papers
INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF 5-NITROPYRIMIDINE WITH ENAMINES. SYNTHESIS OF 3-NITROPYRIDINE DERIVATIVES
Marcelis, Antonius T. M.,Plas, Henk C. van der
, p. 2693 - 2702 (2007/10/02)
The reaction of cyclic and non-cyclic enamines with 5-nitropyrimidine has been studied.Many enamines react in an inverse electron-demand Diels-Alder reaction, leading to the formation of 3-nitropyridines.N,S-ketene acetals were also found to react with 5-nitropyrimidines.The mechanism of the reaction will be discussed.
A new and convenient method for the amination of 1,6- and 1,7-naphthyridines using potassium amide/liquid ammonia/potassium permanganate
Wozniak, M.,Plas, H. C. van der,Tomula, M.,Veldhuizen, A. van
, p. 359 - 363 (2007/10/02)
Treatment of 3-nitro-1,6-naphthyridine, its 2-chloro-, 2-ethoxy- and 2-amino derivatives, with liquid ammonia, containing potassium permanganate, gave the corresponding 2-X-4-amino-3-nitro-1,6-naphthyridines (X=H, Cl, OEt, NH2).From 1H NMR spectroscopy sound evidence for the intermediacy of 2-X-4-amino-1,4-dihydro-3-nitro-1,6-naphthyridine is obtained.Similarly, from 5,8-dichloro(dibromo)-1,7-naphthyridine, the corresponding 2-amino-5,8-dichloro(dibromo)-1,7-naphthyridines were formed on treatment with liquid ammonia/potassium amide/potassium permanganate. 1H NMR evidence for the intermediary C-2 ?-adduct has been obtained.
