Naphthyridines quantum chemical calculations

Also, the observed highly regioselective course in the SnFI substitutions in 2-R-3-nitro-l, 8-naphthyridines (R = FI, OFI, Cl, NFI2, OEt) with the anion of chloromethyl phenyl sulfone was explained by MNDO quantum-chemical calculations showing that, like in the aminations, the interaction of FIOMO of the nucleophile with LUMO of the nitronaphthyridines controls the regioselectivity (91JFIC1075). 

Dinitro[l,8]naphthyridine and its 2-substituted derivatives are dehydro-methylaminated with a solution of potassium permanganate in liquid methylamine to afford the corresponding mono- or bis-methylamino-3,6-dinitro[l,8]naphthyridines (Scheme 7) <2000CJC950>. When the 2-substituent is either chlorine or OMe, then some substitution by NHCH3 also occurs. Quantum-chemical calculations have shown that the reaction is controlled by the interaction of the frontier MOs. 

Substituted 3-nitro-l,8-naphthyridines 349 with chloromethylphenyl sulfone produce 3-nitro-4-(phenylsulfonylmethyl)-l,8-naphthyridines 408 in high yields. Quantum-chemical calculations by the MNDO method demonstrated that the pathway, like that of amination, is determined not by charge control but by the interaction between the HOMO of the nucleophile and the LUMO of the substrate (1991JHC1075). 

During the past 20 years several groups of workers19-28 have carried out quantum mechanical calculations on the naphthyridines and have correlated the results with various chemical and physical properties. 

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