5,6-dibromo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one | 624723-95-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 5,6-dibromo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one
• 英文别名: 5,6-dibromoimidazo[4,5-b]pyridin-2-one；5,6-dibromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one；5,6-dibromo-1,3-dihydroimidazo[4,5-b]pyridin-2-one
• CAS: 624723-95-1
• 化学式: C₆H₃Br₂N₃O
• 分子量: 292.917
• InChiKey: MDLOQBRJBFTQCL-UHFFFAOYSA-N

物化性质

• 熔点：
  >360 °C
• 沸点：
  246.5±40.0 °C(Predicted)
• 密度：
  2?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,6-dibromo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one 在 硫酸 、 potassium nitrate 作用下， 反应 3.5h， 以37%的产率得到6-bromo-5-nitro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one
  参考文献：
  名称：

  1,3-二氢-2H-咪唑并[4,5-b]吡啶-2-酮衍生物的硝化

  摘要：

  Nitration of 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one and its N-methyl derivatives at 0-5 degrees C and 60 degrees C gives 5-nitro- and 5,6-dinitro-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones, respectively. The latter can also be obtained by nitration of 5-mononitro derivatives under similar conditions. The nitration of 6-chloro- and 6-bromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones and their N-methyl-substituted analogs leads to the formation of the corresponding 6-chloro(bromo)-5 -nitro compounds. The same products are formed in the nitration of 5,6-dichloro- and 5,6-dibromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones. In this case, the process involves replacement of the halogen atom in position 5 of the pyridine fragment by nitro group. The nitration of 6-bromo-5-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one is accompanied by oxidation of the 5-methyl group to carboxy.

  DOI：

  10.1134/s1070428007030153
• 作为产物：
  描述：

  1,3-二氢咪唑并[4,5-b]吡啶-2-酮 在 溴 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 以78%的产率得到5,6-dibromo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one
  参考文献：
  名称：

  Halogenation of Imidazo[4,5-b]pyridin-2-one Derivatives

  摘要：

  在醋酸中，以90–95°C对2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮及其N-甲基取代衍生物进行氯化和溴化，会形成相应的5,6-二氯（或二溴）-2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮。在类似条件下，使用ICl对相同底物进行碘化会生成6-碘衍生物。对6-碘-1,3-二甲基-2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮进行氯化时，碘原子被氯取代，生成5,6-二氯-1,3-二甲基-2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮。对6-溴和6-氯-2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮进行溴化分别得到5,6-二溴-和5-溴-6-氯-2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮。

  DOI：

  10.1007/s11178-005-0206-y

文献信息

• Halogenation of 2-Unsubstituted and 2-Methylimidazo[4,5-b]pyridine Derivatives
  作者：Yu. M. Yutilov、Kh. Ya. Lopatinskaya、N. N. Smolyar、S. V. Gres’ko

  DOI：10.1007/s11178-005-0186-y

  日期：2005.3

  Halogenation of 2-unsubstituted and 2-methylimidazo[4,5-b]pyridines and their N-methyl derivatives with bromine and chlorine in acetic acid takes different pathways, depending on the acetic acid concentration. The bromination in 50% aqueous acetic acid gives only 6-bromoimidazo[4,5-b]pyridines; bromination and chlorination of 2-unsubstituted imidazo[4,5-b]pyridines in glacial acetic acid leads to 5,6-dibromo(dichloro)imidazo[4,5-b]pyridin-2-ones, and bromination of 2-methylimidazo[4,5-b]pyridines in glacial acetic acid involves both the pyridine ring and the 2-methyl group to afford the corresponding 6-bromo-2-tribromomethylimidazo[4,5-b]pyridines.

  在乙酸中用溴和氯对 2-未取代的和 2-甲基咪唑并[4,5-b]吡啶及其 N-甲基衍生物进行卤化，根据乙酸浓度的不同，卤化途径也不同。在 50% 的乙酸水溶液中进行溴化反应只能得到 6-溴咪唑并[4,5-b]吡啶；在冰醋酸中对 2-未取代的咪唑并[4,5-b]吡啶进行溴化和氯化反应，可生成 5,6-二溴（二氯）咪唑并[4,5-b]吡啶-2-酮；在冰醋酸中对 2-甲基咪唑并[4,5-b]吡啶进行溴化反应，可生成 2-甲基咪唑并[4,5-b]吡啶-2-酮、2-甲基咪唑并[4,5-b]吡啶在冰乙酸中的溴化反应涉及吡啶环和 2-甲基，从而得到相应的 6-溴-2-三溴甲基咪唑并[4,5-b]吡啶。
• ——
  作者：Yu. M. Yutilov、Kh. Ya. Lopatinskaya、N. N. Smolyar、I. V. Korol'

  DOI：10.1023/a:1025564908743

  日期：——
• Halogenation of Imidazo[4,5-b]pyridin-2-one Derivatives
  作者：Yu. M. Yutilov、Kh. Ya. Lopatinskaya、N. N. Smolyar、S. V. Gres’ko

  DOI：10.1007/s11178-005-0206-y

  日期：2005.4

  Chlorination and bromination of 2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one and its N-methyl-substituted derivatives in acetic acid at 90–95°C leads to formation of the corresponding 5,6-dichloro(dibromo)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones. Iodination of the same substrates with ICl under analogous conditions yields 6-iodo derivatives. Chlorination of 6-iodo-1,3-dimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one is accompanied by replacement of the iodine atom by chlorine with formation of 5,6-dichloro-1,3-dimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one. Bromination of 6-bromo- and 6-chloro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones gives 5,6-dibromo- and 5-bromo-6-chloro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones, respectively.

  在醋酸中，以90–95°C对2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮及其N-甲基取代衍生物进行氯化和溴化，会形成相应的5,6-二氯（或二溴）-2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮。在类似条件下，使用ICl对相同底物进行碘化会生成6-碘衍生物。对6-碘-1,3-二甲基-2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮进行氯化时，碘原子被氯取代，生成5,6-二氯-1,3-二甲基-2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮。对6-溴和6-氯-2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮进行溴化分别得到5,6-二溴-和5-溴-6-氯-2,3-二氢-1H-咪唑[4,5-b]吡啶-2-酮。
• Nitration of 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one derivatives
  作者：N. N. Smolyar、Kh. Ya. Lopatinskaya、A. B. Vasilechko、D. A. Lomov、Yu. M. Yutilov

  DOI：10.1134/s1070428007030153

  日期：2007.3

  Nitration of 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one and its N-methyl derivatives at 0-5 degrees C and 60 degrees C gives 5-nitro- and 5,6-dinitro-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones, respectively. The latter can also be obtained by nitration of 5-mononitro derivatives under similar conditions. The nitration of 6-chloro- and 6-bromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones and their N-methyl-substituted analogs leads to the formation of the corresponding 6-chloro(bromo)-5 -nitro compounds. The same products are formed in the nitration of 5,6-dichloro- and 5,6-dibromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones. In this case, the process involves replacement of the halogen atom in position 5 of the pyridine fragment by nitro group. The nitration of 6-bromo-5-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one is accompanied by oxidation of the 5-methyl group to carboxy.