Diethyl (5-(chlorocarbonyl)-6,7-difluoro-1H,4H-thiazolo<3,4-a>quinoxalin-1-ylidene)malonate | 158898-79-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: Diethyl (5-(chlorocarbonyl)-6,7-difluoro-1H,4H-thiazolo<3,4-a>quinoxalin-1-ylidene)malonate
• 英文别名: diethyl 2-(5-carbonochloridoyl-6,7-difluoro-4H-[1,3]thiazolo[3,4-a]quinoxalin-1-ylidene)propanedioate
• CAS: 158898-79-4
• 化学式: C₁₈H₁₅ClF₂N₂O₅S
• 分子量: 444.843
• InChiKey: NMYBCNSGCGRNJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Diethyl (5-(chlorocarbonyl)-6,7-difluoro-1H,4H-thiazolo<3,4-a>quinoxalin-1-ylidene)malonate 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 1.17h， 以85%的产率得到Diethyl (6,7-difluoro-1H,4H-thiazolo<3,4-a>quinoxalin-1-ylidene)malonate
  参考文献：
  名称：

  Synthesis of New DNA Gyrase Inhibitors: Application of the DMSO Oxidation to the Conversion of the Amine into the Imine

  摘要：

  A novel type of pyridonecarboxylic acid with a planar thiazolopyrazine-incorporated tetracyclic skeleton, 4,9b-diaza-8,9b-dihydro-6-fluoro-5-(4-methyl-1-piperazinyl)-8-oxo-1-thia-1H-yclopenta[cd]phenalene-9-carboxylic acid (3), was prepared. Compound 3 was a potent inhibitor of DNA gyrase and exhibited attractive antibacterial activity against both Gram-positive and Gram-negative bacteria. In the course of the synthetic studies, we have found a new oxidation method of the amine 4 to the imine 5 with DMSO activated by trifluoroacetic anhydride or oxalyl chloride. The DMSO/trifluoroacetic anhydride method gave the byproduct 8, an unusual (methylthio)methyl adduct. The DMSO/oxalyl chloride method gave the byproducts 9 and 10, a (methylthio)methyl ester, and a halogen adduct, respectively. The mechanisms of these oxidations are also discussed.

  DOI：

  10.1021/jo00099a042
• 作为产物：
  描述：

  1-Chloro-5-chlorocarbonyl-6,7-difluoro-4,5-dihydro-thiazolo[3,4-a]quinoxalin-10-ylium; chloride 、 丙二酸二乙酯 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.58h， 生成 Diethyl (5-(chlorocarbonyl)-6,7-difluoro-1H,4H-thiazolo<3,4-a>quinoxalin-1-ylidene)malonate
  参考文献：
  名称：

  Synthesis of New DNA Gyrase Inhibitors: Application of the DMSO Oxidation to the Conversion of the Amine into the Imine

  摘要：

  A novel type of pyridonecarboxylic acid with a planar thiazolopyrazine-incorporated tetracyclic skeleton, 4,9b-diaza-8,9b-dihydro-6-fluoro-5-(4-methyl-1-piperazinyl)-8-oxo-1-thia-1H-yclopenta[cd]phenalene-9-carboxylic acid (3), was prepared. Compound 3 was a potent inhibitor of DNA gyrase and exhibited attractive antibacterial activity against both Gram-positive and Gram-negative bacteria. In the course of the synthetic studies, we have found a new oxidation method of the amine 4 to the imine 5 with DMSO activated by trifluoroacetic anhydride or oxalyl chloride. The DMSO/trifluoroacetic anhydride method gave the byproduct 8, an unusual (methylthio)methyl adduct. The DMSO/oxalyl chloride method gave the byproducts 9 and 10, a (methylthio)methyl ester, and a halogen adduct, respectively. The mechanisms of these oxidations are also discussed.

  DOI：

  10.1021/jo00099a042

文献信息

• Synthesis of New DNA Gyrase Inhibitors: Application of the DMSO Oxidation to the Conversion of the Amine into the Imine
  作者：Yoshikazu Jinbo、Hirosato Kondo、Masahiro Taguchi、Fumio Sakamoto、Goro Tsukamoto

  DOI：10.1021/jo00099a042

  日期：1994.10

  A novel type of pyridonecarboxylic acid with a planar thiazolopyrazine-incorporated tetracyclic skeleton, 4,9b-diaza-8,9b-dihydro-6-fluoro-5-(4-methyl-1-piperazinyl)-8-oxo-1-thia-1H-yclopenta[cd]phenalene-9-carboxylic acid (3), was prepared. Compound 3 was a potent inhibitor of DNA gyrase and exhibited attractive antibacterial activity against both Gram-positive and Gram-negative bacteria. In the course of the synthetic studies, we have found a new oxidation method of the amine 4 to the imine 5 with DMSO activated by trifluoroacetic anhydride or oxalyl chloride. The DMSO/trifluoroacetic anhydride method gave the byproduct 8, an unusual (methylthio)methyl adduct. The DMSO/oxalyl chloride method gave the byproducts 9 and 10, a (methylthio)methyl ester, and a halogen adduct, respectively. The mechanisms of these oxidations are also discussed.