Nagatoshi Nishiwaki
Kochi University, Japan
Title: Synthesis of versatile aza-heterocyclic compounds by three component ring transformation
Biography
Biography: Nagatoshi Nishiwaki
Abstract
Dinitropyridone 1 is an excellent substrate for the nucleophilic type ring transformation to afford heterocyclic compounds
and nitroanilines those are not easily available by alternative methods. When pyridone 1 was reacted with aromatic ketone
in the presence of NH4OAc, 6-arylated 3-nitropyriines 2 were formed besides bicyclic compounds 3. This method was also
applicable to synthesis of cycloalka[b]pyridines 4 and 6-alkynylated/alkenylated pyridines 5, respectively. It was found to be
possible to use aldehydes as the substrate, which leading to 3,5-disubstituted pyridines 6. On the other hand, when aliphatic
ketones were employed as the substrate, two kinds of ring transformation proceeded. Namely, 2,6-disubstituted 4-nitroanilines
8 were formed in addition to nitropyridines 7. It was successful to apply this protocol to synthesis of N,N,2,6-tetrasubstituted
nitroanilines 9 upon treatment of dinitropyridone 1 with ketone and amine in the presence of acetic acid.