Abstract
Nitro compounds show great importance in chemistry, biology and material sciences. Among them, nitropyridines and nitroanilines are widely used as useful intermediates for synthesis of biologically active compounds of pharmaceutical and agrochemical importance. Hence, we reported a powerful method for synthesis of various kinds of nitro compounds by using a three component ring transformation (TCRT) of dinitropyridone 1 with ketones in the presence of less nucleophilic ammonium acetate (NH4OAc) as nitrogen source. When pyridone 1 was reacted with aromatic ketone in the presence of ammonium acetate, 6-arylated 3-nitropyriines 2 were formed besides diazabicyclo compounds 3. This method was also applicable to cycloalkanones and α,β-unsaturated ketones to afford cycloalka[b]pyridines 4 and 6-alkynylated/alkenylated pyridines 5, respectively. It was found to be possible to use aldehydes as the substrate, what led 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. This protocol was successful applied 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.
Highlights
Functionalized Heterocyclic Compounds are Useful for Medicines, Agricultural Chemicals, Dyes, Organic Electroluminescence etc.It is not Easy to Functionalize the Heterocyclic Framework.Efficient Functionalization Method should be Developed.Ring Transformation is One of the Solution for This Problem !!What is the Ring Transformation? Scrap & Built Diels-Alder Type Degenerate TypeNewType Ring Transformation (Nucleophilic Type)Electron-DeficiencySubstrate Should Have and
When pyridone 1 was reacted with aromatic ketone in the presence of ammonium acetate, 6-arylated 3-nitropyriines 2 were formed besides diazabicyclo compounds 3
This method was applicable to cycloalkanones and α,βunsaturated ketones to afford cycloalka[b]pyridines 4 and 6alkynylated/alkenylated pyridines 5, respectively
Summary
Functionalized Heterocyclic Compounds are Useful for Medicines, Agricultural Chemicals, Dyes, Organic Electroluminescence etc.It is not Easy to Functionalize the Heterocyclic Framework.Efficient Functionalization Method should be Developed.Ring Transformation is One of the Solution for This Problem !!What is the Ring Transformation? Scrap & Built Diels-Alder Type Degenerate TypeNewType Ring Transformation (Nucleophilic Type)Electron-DeficiencySubstrate Should Have and. * Corresponding author: nishiwaki.nagatoshi@kochi-tech.ac.jp via Three Component Ring Transformation Abstract: A file syntheis of nitropyridines and nitroanilines are achieved by using a three component ring transformation of dinitropyridone 1 with ketones in the presence of less nucleophilic ammonium acetate (NH4OAc) as nitrogen source. When pyridone 1 was reacted with aromatic ketone in the presence of ammonium acetate, 6-arylated 3-nitropyriines 2 were formed besides diazabicyclo compounds 3.
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