Pyridone 1-methyl-3,5-dinitro

Nitroenamines and related compottnds have been used for synthesis of a variety of heterocyclic compottnds. Rajappahassummaiized the chemistry of nltroenamines fseeSecdon4.2. Anga and coworkers have developed the synthesis of heterocycles based on the reacdon of nltropytidones or nltropyrimldmone v/ith nucleophiles. For example, 2-subsdntted 3-nltro-pyridmes are obtained by the reacdon of l-methyl-3,5-dinitro-2-pyridones wiih ketones in the presence of ammonia fEq. 10.82. ... 

In order to clarify the reaction mechanism, 6-deuterio-labeled 3,5-dinitro-l-methyl-2-pyridone (87, 1 mmol) was prepared and heated with cyclohexanone (2 mmol) and ammonia (10 mmol). A mixture of 2-deuterio- (88) and 4-deuterio-3-nitro-5,6,7,8-tetrahydroquinoline (89) was obtained in the ratio 58 42 (Scheme III.49). 

Nitration of 2-pyridone, originally thought to give mainly 3-nitro-2-pyridone (47) together with some 3,5-dinitro-2-pyridone (48) and a trace of the 5-nitro derivative (49),123 was later shown to give a mixture of 47 and 48.124 Similarly, reaction of 6-methyl-2-pyridone with nitric acid in glacial acetic acid gave the product of nitration at C-3 (50).125 This preferential ortho-nitration is in marked contrast to... 

Nitration of p-cymene by fuming nitric add leads to 2,4-dinitrotoluene.1184 Heating 1,6-dihydro-l-methyl-6-oxonicotinic acid with nitric acid (d 1.52) under reflux gives 1-methyl-3,5-dinitro-2(li/)-pyridone in good yield.1185 2,6-Dibromo-4-nitrosophenol is formed quantitatively from 3,5-dibromo-4-hydroxybenzoic acid and sodium nitrite in aqueous alcohol.166,1183 Nitrous acid replaces hydroxymethyl groups in phenols by nitro groups,1186 and diazonium salts replace them by diazo groups.1187... 

Mixtures of 3- and 5-nitro-4-methyl-2-pyridone and of 3- and 5-nitro-6-methyl-2-pyridone have been converted to the corresponding 3,5-dinitro-2-pyridones with nitric acid in oleum. ... 

---