2-methoxy-(1H)-quino[4,3-e]-1,2,4-thiadiazine 4,4-dioxide | 1338227-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 2-methoxy-(1H)-quino[4,3-e]-1,2,4-thiadiazine 4,4-dioxide
• 英文别名: 3-methoxy-(1H)-quino[4,3-e]-1,2,4-thiadiazine 4,4-dioxide；2-methoxy-1H-[1,2,4]thiadiazino[6,5-c]quinoline 4,4-dioxide
• CAS: 1338227-74-9
• 化学式: C₁₁H₉N₃O₃S
• 分子量: 263.277
• InChiKey: LZWKFYPBCMVQMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methoxy-(1H)-quino[4,3-e]-1,2,4-thiadiazine 4,4-dioxide 在 potassium methanolate 、 三乙胺盐酸盐 、 二氯磷酸苯酯 、 正丁胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 2-butylamino-6-methyl-(6H)-quino[4,3-e]-1,2,4-thiadiazine 4,4-dioxide
  参考文献：
  名称：

  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

  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 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.

  DOI：

  10.3987/com-11-12247
• 作为产物：
  描述：

  4-氯-3-喹啉磺酰氯 在 caesium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 19.0h， 生成 2-methoxy-(1H)-quino[4,3-e]-1,2,4-thiadiazine 4,4-dioxide
  参考文献：
  名称：

  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

  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 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.

  DOI：

  10.3987/com-11-12247

文献信息

• Synthesis and Transformations of 2-Oxo-2,3-dihydro-(1H,3H)-quino[4,3-e]-1,2,4-thiadiazine 4,4-Dioxide to N-Methyl-, 2-Chloro- and 2-Aminoquino[4,3-e]-1,2,4-thiadiazine 4,4-Dioxides
  作者：Elwira Chrobak、Stanisław Boryczka、Michał Wlekliński、Joachim Kusz、Maciej Zubko、Andrzej Maślankiewicz

  DOI：10.3987/com-15-13309

  日期：——

  Fusion of 4-amino-3-quinolinesulfonamide (1a) with urea and N-methyl- and N,N'-dimethylurea resulted in 2-oxo-2,3-dihydro-(1H,3H)quino[4,3-e]-1,2,4-thiadiazine 4,4-oxide (3a). Reaction of thiadiazinone 3a with a MeI/MeOK/DMF system gave a mixture of the 3-methyl derivative 3c (major product) and 6-methyl derivative 3d (minor product), and the mixture of 3c and 3d could be methylated with the same system as above to afford the 3,6-dimethyl derivative 3e. Chlorination of 3a with P(O)Cl-3/phosphoric acid system performed in the presence of pyridine hydrochloride resulted in zwitterionic pyridinio-quinothiadiazinate 7 (63%) accompanied by 2-chloroquinothiadiazine 6 (15%), and the same reaction performed with the use of triethylamine hydrochloride gave the expected chloroquinothiadiazine 6 (73%). Chloro derivative 6 was then aminated to 2-aminoquinothiadiazines 8a,b,c.