4-(2-azidophenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one | 1248635-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(2-azidophenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: 4-(2-azidophenyl)-3,4-dihydropyrimidin-2-one；ethyl 4-(2-azidophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 1248635-13-3
• 化学式: C₁₄H₁₅N₅O₃
• 分子量: 301.305
• InChiKey: IDESTNHOZUSXQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-azidophenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one 以 二甲基亚砜 为溶剂， 反应 6.0h， 以82%的产率得到ethyl 4-methylene-2-oxo-2,3,4,4a,5,9b-hexahydro-1H-pyrimido[5,4-b]indole-4a-carboxylate
  参考文献：
  名称：

  Photochemical and thermal cyclizations of 4-(2-azidophenyl)-3,4-dihydropyrimidin-2-ones for the synthesis of 4-methylenepyrimidino[5,4-b]indol-2-ones

  摘要：

  Photochemical and thermal cyclization of 4-(2-azidophenyl)-3,4-dihydropyrimidin-2-ones could afford fused indoles, such as 1,2,3a,9b-tetrahydro-4-methylenepyrimidino[5,4-b]indol-2-ones and 1,3,5,6,7a, 12b-hexahydroquinazolino[9,4-b]indol-2,7-dione in high yields via nitrene electrophilic addition and rearrangement reactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.176
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 2-叠氮基苯甲醛 、 尿素 在 三甲基氯硅烷 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 以92%的产率得到4-(2-azidophenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  New efficient synthesis of pyrimido[1,6-c]quinazolin-4-ones by a Biginelli 3CC/Staudinger/aza-Wittig sequence

  摘要：

  Dihydropyrimidinone azides 1, obtained from trimethylsilyl chloride-catalyzed Biginelli reaction of 2-azidobenzaldehyde, ethyl acetoacetate, and urea (or thiourea) at room temperature, reacted with triphenylphosphine to give iminophosphorane 2. A tandem aza-Wittig reaction of iminophosphorane 2 with isocyanate, acyl chloride or CS2 in the presence of K2CO3 or NEt3 generated pyrimido[1,6-c]quinazolin-4-ones 4, 6 or 8 in moderate to good yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.046

文献信息

• New efficient synthesis of pyrimido[1,6-c]quinazolin-4-ones by a Biginelli 3CC/Staudinger/aza-Wittig sequence
  作者：Wen-Jing Li、Shuai Liu、Ping He、Ming-Wu Ding

  DOI：10.1016/j.tet.2010.08.046

  日期：2010.10

  Dihydropyrimidinone azides 1, obtained from trimethylsilyl chloride-catalyzed Biginelli reaction of 2-azidobenzaldehyde, ethyl acetoacetate, and urea (or thiourea) at room temperature, reacted with triphenylphosphine to give iminophosphorane 2. A tandem aza-Wittig reaction of iminophosphorane 2 with isocyanate, acyl chloride or CS2 in the presence of K2CO3 or NEt3 generated pyrimido[1,6-c]quinazolin-4-ones 4, 6 or 8 in moderate to good yield. (C) 2010 Elsevier Ltd. All rights reserved.
• Photochemical and thermal cyclizations of 4-(2-azidophenyl)-3,4-dihydropyrimidin-2-ones for the synthesis of 4-methylenepyrimidino[5,4-b]indol-2-ones
  作者：Yu-wei Ren、Xuerui Wang、Weixia Wang、Bing Li、Zong-jun Shi、Wei Zhang

  DOI：10.1016/j.tetlet.2010.10.176

  日期：2011.1

  Photochemical and thermal cyclization of 4-(2-azidophenyl)-3,4-dihydropyrimidin-2-ones could afford fused indoles, such as 1,2,3a,9b-tetrahydro-4-methylenepyrimidino[5,4-b]indol-2-ones and 1,3,5,6,7a, 12b-hexahydroquinazolino[9,4-b]indol-2,7-dione in high yields via nitrene electrophilic addition and rearrangement reactions. (C) 2010 Elsevier Ltd. All rights reserved.