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Paper | Regular issue | Vol 81, No. 8, 2010, pp.1799-1810
Published online, 21st June, 2010
DOI: 10.3987/COM-10-11963
■ 2-Methyl- and 2-Dimethylaminoquino[4,3-e]-1,2,4-thiadiazine 4,4-Dioxides – Synthesis, Structure and N-Methylation

Elwira Chrobak, Michał Wlekliński, Andrzej Maślankiewicz,* Joachim Kusz, Maciej Zubko, and Andrzej Zięba

*Department of Organic Chemistry, The Medical University of Silesia, Jagielloñska Str. 4, 41-200 Sosnowiec, Poland

Abstract

Reaction of 4-chloro-3-quinolinesulfonyl chloride (1) with acetamidine or with N,N-dimethyl- and N,N,N'-trimethylquanidine salts led directly or stepwise via 4-chloro-3-quinolinesulfonylguanidine (6a) to the title 2-substituted quino[4,3-e]-1,2,4-thiadiazine 4,4-dioxides (4, 7a, and 8). X-Ray studies proved that 2-methyl derivative 4 exists as the 1H-tautomer while 2-dimethylamino derivative 7a as the 6H-tautomer. Reaction of N-H derivatives 4 and 7a and the pyrido-1,2,4-thiadiazine analog 11a with CH3I/CH3OK/DMF system proceeded at the pyridine-ring nitrogen and led to 6-methylquino derivatives 5 and 7b or the 7-methylpyrido derivative 11b, respectively, as concluded from 2D 1H - 13C NMR data.