ethyl 3-(azidomethyl)-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 1254330-84-1

• 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: ethyl 3-(azidomethyl)-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• CAS: 1254330-84-1
• 化学式: C₁₅H₁₇N₅O₃
• 分子量: 315.332
• InChiKey: DJECRYOTVVYRLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  107.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(azidomethyl)-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate 、 苯乙炔 在 copper(l) iodide 作用下， 以 水 为溶剂， 反应 6.0h， 以64%的产率得到ethyl 6-methyl-2-oxo-4-phenyl-3-[(4-phenyl-1H-1,2,3-triazol-1-yl)methyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  一锅四组分反应通过铜催化点击合成具有3,4-二氢嘧啶酮或酰胺基的功能化1,2,3-三唑

  摘要：

  由Cu（OAc）2 ·H 2 O /抗坏血酸钠原位生成的Cu（I）催化一锅多组分反应，用于合成一系列N官能化的1,2,3-三唑与3,4-二氢嘧啶酮描述了由3，4-二氢嘧啶酮，低聚甲醛，叠氮化钠和炔烃组成的化合物。通过该方法制备了具有酰胺的显着N-官能化的1,2,3-三唑。此过程无需处理有机卤化物或有机叠氮化物，因为它们是在原位生成的，因此这种本已强大的点击过程更加人性化和安全。

  DOI：

  10.1016/j.tet.2012.10.097
• 作为产物：
  描述：

  聚合甲醛 、 6-甲基-2-氧代-4-苯基-1,2,3,4-四氢-5-嘧啶羧酸乙酯 在 三甲基氯硅烷 、 sodium azide 作用下， 以 二氯甲烷 为溶剂， 反应 32.0h， 以72%的产率得到ethyl 3-(azidomethyl)-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  One-Pot Two-Step Synthesis of N3-Functionalized 3,4-Dihydropyrimidinones in the Presence of TMSCl

  摘要：

  Novel 3,4-dihydropyrimidinones modified with N3-alkyloxymethyl, aminomethyl, arylsulfonylmethyl, and azidomethyl groups can be regioselectively obtained over their isomeric NI compounds in good yields by reaction of 3,4-dihydropyrimidinones with paraformaldehyde and alcohol, amine, sodium benzenesulfinate, and sodium azide, respectively, by a one-pot two-step strategy in the presence of chlorotrimethylsilane. The advantages of this method are the simple procedure, the high regioselectivity of the products, no requirement for a base catalyst, and the mild reaction conditions.

  DOI：

  10.3987/com-10-11968

文献信息

• PEG-OSO3H as an Efficient Catalyst in the Synthesis of N3-Functionalized 3.4-Dihydropyrimidinone and Quinazolinone Derivatives
  作者：Xi-Cun Wang、Liang-Jie Yang、Jin-Ge Luo

  DOI：10.3987/com-17-13659

  日期：——

  PEG-OSO3H-catalyzed three-component reaction of 3,4-dihydropyrimidones and quinazolinone with paraformaldehyde and various reagents for synthesis of N3-functionalized 3,4-dihydropyrimidone and quinazolinone derivatives is described. 2-Hydroxy-substituted 3,4-dihydropyrimidone reacts with aldehydes giving benzo[e]pyrimido[1,6-c][1,3]oxazines. This paper explores the versatility and effectiveness of polymer bound sulfonic acids as catalysts in different C-N and C-O bonds formation reactions. The reactions were completed in short times, and the products were obtained in good to excellent yields. The catalysts activity and recyclability were investigated completely.