84531-35-1Relevant articles and documents
Synthesis, Characterization, and Rapid Cycloadditions of 5-Nitro-1,2,3-triazine
Glinkerman, Christopher M.,Boger, Dale L.
supporting information, p. 2628 - 2631 (2018/05/17)
The synthesis, characterization, and a study of the cycloaddition reactions of 5-nitro-1,2,3-triazine (3) are reported. The electron-deficient nature of 3 permits rapid cycloaddition with a variety of electron-rich dienophiles, including amidines, enamines, enol ethers, ynamines, and ketene acetals in high to moderate yields. 1H NMR studies of a representative cycloaddition reaction between 3 and an amidine revealed a remarkable reaction rate and efficiency (1 mM, 3CN, 23 °C, >95%).
Nitropyrimidinones; synthetic equivalents of diformylamine and nitromalonaldehyde
Nishiwaki,Tohda,Ariga
, p. 1277 - 1280 (2007/10/03)
Reactions of two isomeric nitropyrimidinones with bidentate enolate anions were studied. When 3-methyl-5-nitropyrimidin-4(3H)-one (1) was employed, ring transformation proceeded to give pyridin-4(1H)-ones 3 functionalized at the 3- or 5-positions. This pyrimidin-4-one 1 behaved as an activated diformylamine HN(CHO)2. 1-Methyl-5-nitropyrimidin-2(1H)-one (2) afforded polyfunctionalized bicyclo[3.3.1]nonene derivatives 7 and 8 and/or p-nitrophenol derivatives 9. In this case, pyrimidin-2-one 2 acted as the synthetic equivalent of unstable O2NCH(CHO)2. These two nitropyrimidinones are valuable intermediates for the synthesis of polyfunctionalized compounds.
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.