5-amino-1,3-dibenzyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one | 893725-46-7

• 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-amino-1,3-dibenzyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one
• 英文别名: 5-amino-1,3-dibenzyl-1H,2H,3H-imidazo[4,5-b]pyridin-2-one；5-amino-1,3-dibenzylimidazo[4,5-b]pyridin-2-one
• CAS: 893725-46-7
• 化学式: C₂₀H₁₈N₄O
• mdl: MFCD07364242
• 分子量: 330.389
• InChiKey: KMFUEJHDIXKEPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  62.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-二甲基-4-吡喃酮 、 5-amino-1,3-dibenzyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one 以 溶剂黄146 为溶剂， 反应 6.0h， 以68%的产率得到5-{2,6-dimethyl-4-[(1,3-dibenzyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)imino]-pyridin-1(4H)-yl}-1,3-dibenzyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one
  参考文献：
  名称：

  Condensation of amino derivatives of benzimidazol-2-ones and imidazo[4,5-b]pyridin-2-ones with 2,6-dimethyl-γ-pyrone in acetic acid

  摘要：

  DOI：

  10.1134/s107042801305031x
• 作为产物：
  描述：

  1,3-dibenzyl-5-nitro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one 在 一水合肼 作用下， 反应 14.0h， 以74%的产率得到5-amino-1,3-dibenzyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one
  参考文献：
  名称：

  Synthesis of 1-(1,3-dialkyl-2-oxo-2,3-dihydro-1H-imidazo-[4,5-b]pyridin-5-yl)-5-oxopyrrolidine-3-carboxylic acids

  摘要：

  Nitration of 2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one gave its 5-nitro derivative which was subjected to alkylation with dimethyl sulfate, diethyl sulfate, and benzyl(dimethyl)phenylammonium chloride. The resulting 1,3-dimethyl-, 1,3-diethyl-, and 1,3-dibenzyl-5-nitro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones were reduced to the corresponding 1,3-dialkyl-5-amino-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones, and the latter reacted with itaconic acid to produce 1-(1,3-dialkyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)-5-oxopyrrolidine-3-carboxylic acids. 1-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)-5-oxopyrrolidine-3-carboxylic acid was obtained by analogous reaction with 5-amino-2,3-dihydro-1H-imidazo[4,5-b]-pyridin-2-one.

  DOI：

  10.1134/s1070428007110206

文献信息

• Reactions of 1,3-Dialkyl-5-amino-1,3-dihydro-2H-imidazo-[4,5-b]pyridin-2-ones with acetylacetone and ethyl acetoacetate
  作者：N. N. Smolyar、D. A. Lomov

  DOI：10.1134/s1070428009030129

  日期：2009.3

  1,3-Dialkyl-5-amino-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones reacted with acetylacetone to give the corresponding 4-(1,3-dialkyl-2-oxo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-5-ylamino)pent-3-en-2-ones which underwent intramolecular cyclization to 1,3-dialkyl-5,7-dimethyl-1,3-dihydro-2H-imidazo[4,5-b]-[1,8]naphthyridin-2-ones on heating in polyphosphoric acid or diphenyl ether. Analogous reaction of

  1,3-二烷基-5-氨基-1,3-二氢-2 H-咪唑并[4,5 - b ]吡啶-2-酮与乙酰丙酮反应生成相应的4-（1,3-二烷基-2- oxo-1,3-dihydro-2 H-咪唑并[4,5 - b ]吡啶-5-基氨基）戊-3-en-2-ones，它们经过分子内环化成1,3-二烷基-5,7-二甲基在多磷酸或二苯醚中加热时的-1,3-二氢-2 H-咪唑并[4,5- b ]-[1,8]萘啶-2-酮。1,3-二烷基-5-氨基-1,3-二氢-2 H-咪唑并[4,5 - b ]吡啶-2-酮与乙酰乙酸乙酯的类似反应导致3-（1,3）乙基的形成-二烷基-2-氧代-1,3-二氢-2 H-咪唑[4,5- b] pyridin-5-ylamino）but-2-enoates，其环化生成1,3-二烷基-8-羟基-7-甲基-1,3-二氢-2 H-咪唑[5,4- b ] [1,8 ]萘啶-2-酮。
• Synthesis of 1,3-dialkyl-5-(pyrrol-1-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones
  作者：N. N. Smolyar、D. A. Lomov、Ya. S. Borodkin、S. V. Gresko

  DOI：10.1134/s1070428009050273

  日期：2009.5