Abstract
The complete 1H and 13C NMR characterization of some representative examples of five and six-membered amidinoquinoxaline N-oxides 1 with dissymmetric aryl substituents and their methiodides 2 is reported. Compounds 1 were synthesized by ring closure of N-arylacetyl- N′ -(2-nitrophenyl)alkylenediamines 3, followed by spontaneous heterocyclization. Methiodides 2 were prepared by quaternization of the parent heterocycles with methyl iodide. Complete assignment of the 1H and 13C NMR resonances of compounds 1, 2 was made on the basis of the correlations observed in their HSQC, HMBC and NOESY spectra. The 1H NMR spectra of compounds 1, 2 display diasterotopicity of methylenic hydrogens, indicative of molecular chirality due to the presence of a chiral axis (ONC-Ar bond). Further support for the existence of the atropisomers for compounds 1a, b is presented, on the basis of spectral and theoretical data.
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