PYRIDO- AND QUINO-1,2,4-THIADIAZINE S,S-DIOXIDES FROM REACTIONS OF 4-CHLORO-3-PYRIDINESULFONYL- AND 4-CHLORO-3-QUINOLINESULFONYL CHLORIDES WITH O-METHYLISOUREA

Reaction of 4-chloro-3- pyridine- (or quinoline)sulfonyl chlorides (1) or (6) with O-methylisourea led to 4-chloro-3-pyridinesulfonyl-O-methylisourea (2a) or its quinoline analog 2b, respectively. Compounds 2a and 2b underwent dehydrochlorination to the title methoxy-pyrido or quino[4,3-e]-1,2,4-thi...

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Published inHeterocycles Vol. 83; no. 8; pp. 1819 - 1830
Main Authors Chrobak, Elwira, Wleklinski, Michal, Maslankiewicz, Andrzej, Kusz, Joachim, Zubko, Maciej, Michalik, Ewa
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SUBSTITUENT
3-POSITION
IMPACT
Quinoline and Pyridine
TISSUE SELECTIVITY
Amino-Dechlorination
Chloro-Demethoxylation
1,1-DIOXIDES
Sulfonylisourea
DERIVATIVES
1,2,4-Thiadiazine
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Summary:Reaction of 4-chloro-3- pyridine- (or quinoline)sulfonyl chlorides (1) or (6) with O-methylisourea led to 4-chloro-3-pyridinesulfonyl-O-methylisourea (2a) or its quinoline analog 2b, respectively. Compounds 2a and 2b underwent dehydrochlorination to the title methoxy-pyrido or quino[4,3-e]-1,2,4-thiadiazine S,S-dioxides (3 and 7). X-Ray studies proved that both methoxy derivatives (3 and 7) exist as gamma azine-NH-tautomers. Reaction of N-H derivatives 3 and 7 with CH3I/CH3OK/DMF system proceeded at the pyridine-ring nitrogen and led to 7-methylpyrido derivative 4a or the 6-methylquino derivative 8a, respectively. After treatment with PhOP(O)Cl-2 at 120-150 degrees C compounds 4a or 8a were converted to chloro derivatives 4b or 8b, respectively, which were then transformed to aminothiadiazines 5a,b,c or 9a,b,c.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-11-12247