Abstract
Reactions of hydrogen sulfates of quino- and diquino-annelated 1,4-dithiins 11 and 2 with DMF/hydroxylamine-O-sulfonic acid/Fe++ ion system took place at the α-quinolinyl positions and led to N,N-dimethylcarbamoyl and N-methyl-N-formylaminomethyl derivatives 6, 8, 12 and 7, 9, 13, respectively. The 1H and 13C NMR spectra of N-methyl-N-formylaminomethyl derivatives 7, 9, 13 showed the presence of rotational isomers E and Z regarding to the N-methyl-N-formylaminomethyl substituent. The spectra of 6, 7, 8, 12 and 13 were completely assigned with the use of 1D and 2D NMR techniques. In the case of rotational isomers 7a and 7b, the crucial correlations came from the NOE interaction between the methylene and methyl protons from CH2N(CH3)CHO groups and benzene-rings protons. Synthesis of 2,3-dihydro-1,4-dithiino[6,5-e]quinoline 4-oxide 14 was presented as well.
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