1-(2-chlorophenyl)-5-oxo-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carbonitrile | 1448421-76-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(2-chlorophenyl)-5-oxo-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carbonitrile
• 英文别名: 1-(2-Chlorophenyl)-5-oxo-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carbonitrile
• CAS: 1448421-76-8
• 化学式: C₁₃H₉ClN₄O
• 分子量: 272.694
• InChiKey: ZPMQGRYDQCOCOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  59.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  、 2-氰基-3-乙氧基丙烯酸乙酯 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 10.25h， 以60%的产率得到1-(2-chlorophenyl)-5-oxo-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carbonitrile
  参考文献：
  名称：

  The pseudo-Michael reaction of 1-aryl-4,5-dihydro-1H-imidazol-2-amines with ethyl ethoxymethylenecyanoacetate

  摘要：

  The pseudo-Michael reaction of 1-aryl-4,5-dihydro-1H-imidazol-2-amines with ethyl 2-cyano-3-methoxyprop-2-enoate (ethyl ethoxymethylenecyanoacetate) is investigated. At -10 A degrees C reaction takes place on the exocyclic nitrogen atom, giving exclusively ethyl esters of 2-cyano-3-[(1-phenyl-4,5-dihydro-1H-imidazol-2-yl)amino]prop-2-enoic acid. The formation of isomeric enamines which may be a theoretical product of the reaction on N3 ring nitrogen atom is not observed. The N6 enamines, heated in boiling acetic acid, yield cyclic 1-aryl-5-oxo-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carbonitriles. Heating of the enamines to the temperature of 120-140 A degrees C without a solvent makes it possible to obtain a mixture of 1-aryl-5-oxo-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carbonitriles and ethyl 1-aryl-5-imino-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carboxylates. The reaction of the respective hydrobromides of 1-aryl-4,5-dihydro-1H-imidazol-2-amines with ethyl ethoxymethylenecyanoacetate in the presence of triethylamine gives selectively 1-aryl-5-oxo-1,2,3,5-dihydroimidazo[1,2-a]pyrimidine-6-carbonitriles.

  DOI：

  10.1007/s00706-013-0982-y

文献信息

• The pseudo-Michael reaction of 1-aryl-4,5-dihydro-1H-imidazol-2-amines with ethyl ethoxymethylenecyanoacetate
  作者：Agnieszka A. Kaczor、Urszula Kijkowska-Murak、Kalevi Pihlaja、Jari Sinkkonen、Waldemar Wysocki、Zbigniew Karczmarzyk、Dariusz Matosiuk

  DOI：10.1007/s00706-013-0982-y

  日期：2013.8

  The pseudo-Michael reaction of 1-aryl-4,5-dihydro-1H-imidazol-2-amines with ethyl 2-cyano-3-methoxyprop-2-enoate (ethyl ethoxymethylenecyanoacetate) is investigated. At -10 A degrees C reaction takes place on the exocyclic nitrogen atom, giving exclusively ethyl esters of 2-cyano-3-[(1-phenyl-4,5-dihydro-1H-imidazol-2-yl)amino]prop-2-enoic acid. The formation of isomeric enamines which may be a theoretical product of the reaction on N3 ring nitrogen atom is not observed. The N6 enamines, heated in boiling acetic acid, yield cyclic 1-aryl-5-oxo-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carbonitriles. Heating of the enamines to the temperature of 120-140 A degrees C without a solvent makes it possible to obtain a mixture of 1-aryl-5-oxo-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carbonitriles and ethyl 1-aryl-5-imino-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carboxylates. The reaction of the respective hydrobromides of 1-aryl-4,5-dihydro-1H-imidazol-2-amines with ethyl ethoxymethylenecyanoacetate in the presence of triethylamine gives selectively 1-aryl-5-oxo-1,2,3,5-dihydroimidazo[1,2-a]pyrimidine-6-carbonitriles.