Derivatives of some cyclic 3,4-quinolinediyl bis-sulfides with N,N-dimethylcarbamoyl and N-methyl-N-formylaminornethyl substituents in the 2-quinolinyl position

✍ Scribed by Andrzej Maślankiewicz; Ewa Michalik

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2005
• Tongue: English
• Weight: 171 KB
• Volume: 42
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570420619

✦ Synopsis

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 and7, 9, 13, respectively. The 1 H and 13 C 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 CH 2 N(CH 3 )CHO groups and benzene-rings protons. Synthesis of 2,3-dihydro-1,4dithiino[6,5-c]quinoline 4-oxide 14 was presented as well.