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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

  作者 CHROBAK ELWIRA; WLEKLINSKI MICHAL; MASLANKIEWICZ ANDRZEJ; KUSZ JOACHIM; ZUBKO MACIEJ; MICHALIK EWA  
  选自 期刊  Heterocycles;  卷期  2011年83-8;  页码  1819-1830  
  关联知识点  
 

[摘要]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 CH(3)I/CH(3)OK/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.

 
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