Mina Tamura

Novel functionalization of 1-methyl-2-quinolone; dimerization and denitration of trinitroquinolone

New methods for functionalization of 1-methyl-2-quinolone (MeQone) skeleton are provided. The reaction of 1-methyl-3,6,8-trinitro-2-quinolone (TNQ) with amines affords quinolone dimer 1 and 6,8-dinitroquinolone (6,8-DNQ). Dimerization predominantly proceeds at room temperature, and denitration takes place under heated and diluted conditions. We also provide a plausible mechanism for these reactions on the basis of structure–reactivity relationship of amines.

Reaction of 3,5-Dicyanoisoxazoles with Nucleophiles

Cyano groups on 3,5-dicyanoisoxazole readily caused nucleophilic addition of alcohols (or amines) to give corresponding imidates (or amidines). Dicyanoisoxazoles was also converted to 3,5-bis(imidazolinyl)isoxazoles upon treatment with 1,2-diamines.

The Ring Transformation of 3-Methyl-5-nitropyrimidin-4(3H)- one

3-Methyl-5-nitropyrimidin-4(3H)-one readily reacts with carbonyl compounds to produce three kinds of ring transformations. The nitropyrimidinone behaves as the synthetic equivalent of activated diformylamine affording 3,5-difunctionalized 4-pyridones, 4,5-disubstituted pyrimidines and functionalized 4-aminopyridines. It also behaves like α-nitro-formylacetic acid to give 5,6-disubstituted 3-nitro-2-pyridones.

A NOVEL RING TRANSFORMATION OF NITROPYRIMIDINONE LEADING TO POLYFUNCTIONALIZED PYRIDONES

Polyfunctionalized 2-pyridones are readily prepared by the ring transformation using 3-methyl-5-nitropyrimidin-4(3H)-one with active methylene compounds in the presence of piperidine.

Facile synthesis of functionalized 4-aminopyridines

The title compounds are readily available by ring transformation of nitropyrimidione with active methylene compounds in the presence of ammonium acetate.