767567-84-0Relevant articles and documents
Silver(I)-Promoted ipso-Nitration of Carboxylic Acids by Nitronium Tetrafluoroborate
Natarajan, Palani,Chaudhary, Renu,Venugopalan, Paloth
, p. 10498 - 10504 (2015)
A novel and efficient method for the regioselective nitration of a series of aliphatic and aromatic carboxylic acids to their corresponding nitro compounds using nitronium tetrafluoroborate and silver carbonate in dimethylacetamide has been described. This transformation is believed to proceed via the alkyl-silver or aryl-silver intermediate, which subsequently reacts with the nitronium ion to form nitro substances. Mild reaction conditions, tolerant of a broad range of functional groups, and formation of only the ipso-nitrated products are the key features of this methodology when compared to known methods for syntheses of nitroalkyls and nitroarenes.
Nucleophilic reaction upon electron-deficient pyridone derivatives. XIII. Regioselective synthesis of 2-substituted 3-nitropyridines by one-pot reaction of either 4- or 6-substituted 1-methyl-3,5-dinitro-2-pyridones with ketones and ammonia
Tohda,Kawahara,Eiraku,Tani,Nisiwaki,Ariga
, p. 2176 - 2186 (2007/10/02)
A one-pot synthesis of 2-substituted 3- nitropyridines was developed by a ring transformation of 6- or 4-substituted 1-methyl-3,5-dinitro-2-pyridones (2 or 3) with ammonia and enamines derived from ketones. Some intermediates having a 2,6-diazabicyclo[3.3.1]nonane skeleton were isolated from reactions of 3. The ring transformation proceeds via an addition-addition-elimination-elimination mechanism. Few competitive isomeric by-products, 4-substituted 3-nitropyridines and 4-nitroanilines, were formed. All the 2 substrates showed good reactivity, but the 3 substrates having electron-withdrawing substituents were less reactive and selective. 1,4,6-Trimethyl-3,5-dinitro-2-pyridone did not give any products. The selectivity is interpreted in terms of differences of thermodynamic (main selection rule B) and kinetic stability (minor selection rule A) between the possible bicyclic intermediates which are expected to be formed via the mechanism.
REGIOSELECTIVE SYNTHESIS OF 2-SUBSTITUTED 3-NITROPYRIDINES BY ONE-POT REACTION OF EITHER 4- OR 6-SUBSTITUTED 1-METHYL-3,5-DINITRO-2-PYRIDONES WITH KETONES AND AMMONIA
Tohda, Yasuo,Kawara, Tooru,Eiraku, Miyuki,Tani, Keita,Ariga, Masahiro,Mori, Yutaka
, p. 2079 - 2082 (2007/10/02)
Regioselective synthesis of 2-substituted 3-nitropyridines was achieved by one-pot reaction of either 4- or 6-substituted 1-methyl-3,5-dinitro-2-pyridones with ketones in the presence of ammonia.The selectivity is interpreted in terms of steric factor of substituent on the pyridone.