4-(3-nitrophenyl)-2-methyl-1,4-dihydro-benzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxylic acid ethyl ester | 695198-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-(3-nitrophenyl)-2-methyl-1,4-dihydro-benzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxylic acid ethyl ester
• 英文别名: 4-(3-nitrophenyl)-2-methyl-1,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxylic acid ethyl ester；ethyl 2-methyl-4-(3-nitrophenyl)-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate
• CAS: 695198-86-8
• 化学式: C₂₀H₁₈N₄O₄
• 分子量: 378.387
• InChiKey: VZISHCGFFPMHEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氨基苯并咪唑 、 乙酰乙酸乙酯 、 间硝基苯甲醛 在 4,4'-(butane-1,4-diyl)bis(1-sulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium) tetrachloride 作用下， 以 neat (no solvent) 为溶剂， 反应 0.58h， 以92%的产率得到4-(3-nitrophenyl)-2-methyl-1,4-dihydro-benzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  纳米级NS-C 4（DABCO-SO 3 H）2）·4Cl催化高效合成苯并[2,1-b]喹唑啉酮和三唑[2,1-b]喹唑啉酮

  摘要：

  在这项研究中，4,4'-（butane-1,4-diyl）bis（1-sulfo-1,4-diazabicyclo [2.2.2] octane-1,4-diium）tetrachloride（NS-C 4（DABCO -SO 3 H）2）·4Cl用作纳米级布朗斯台德酸催化剂，可高效，优选地合成苯并[2,1- b ]喹唑啉酮和三唑并[2,1- b ]喹唑啉酮衍生物。该方案具有许多优点，包括温和的反应条件，可接受的反应时间，高收率和产物的后处理容易以及催化剂的可重复使用性。

  DOI：

  10.1007/s13738-017-1164-3

文献信息

• Poly(vinylpyrrolidonium) perchlorate catalyzed one-pot synthesis of tricyclic dihydropyrimidine derivatives
  作者：Masoumeh Abedini、Farhad Shirini、Maryam Mousapour、Omid Goli Jolodar

  DOI：10.1007/s11164-016-2456-4

  日期：2016.7

  A simple and efficient procedure for the synthesis of benzo[4,5]imidazo[1,2-α]pyrimidine and 2-amino-4-substituted-1,4-dihydrobenzo[4,5]imidazolo[1,2-α]pyrimidine-3-carbonitrile derivatives using poly(vinylpyrrolidonium) perchlorate [PVPH]ClO4} as a newly reported, modified polymeric catalyst is reported. Some of the advantages of this novel synthetic method are: easy preparation of the catalyst,

  一种简单有效的合成苯并[4,5]咪唑并[1,2- α ]嘧啶和2-氨基-4-取代的1,4-二氢苯并[4,5]咪唑并[1,2- α]的方法报道了使用聚（乙烯基吡咯烷鎓）高氯酸盐[PVPH] ClO 4 }作为新报道的改性聚合物催化剂的嘧啶-3-腈衍生物。这种新颖的合成方法的一些优点是：容易制备催化剂，简单且容易进行后处理，反应时间短，产物的产率高至优异以及催化剂的可重复使用性。
• Microwave-assisted efficient synthesis of benzo[4,5]imidazo[1,2-a]-pyrimidine derivatives in water under catalyst-free conditions
  作者：Shujiang Tu、Qingqing Shao、Dianxiang Zhou、Longji Cao、Feng Shi、Chunmei Li

  DOI：10.1002/jhet.5570440625

  日期：2007.11

  2-a]pyrimidine derivatives were synthesized via the three-component reaction of aldehyde, β-dicarbonyl compound and 2-aminobenzimidazole in water under microwave irradiation and without catalyst conditions. The new protocol has the advantages of higher yield, lower cost, reduced environment impact, wider scope and convenient procedure.

  苯并[4,5]咪唑并[1,2- a ]嘧啶衍生物是通过醛，β-二羰基化合物和2-氨基苯并咪唑在微波辐射下且无催化剂条件下在水中进行三组分反应而合成的。新协议具有产量高，成本低，对环境影响小，适用范围广，操作方便等优点。
• Nano-Co-[4-chlorophenyl-salicylaldimine-pyranopyrimidine dione]Cl2 as a new Schiff base complex and catalyst for the one-pot synthesis of some 4H-pyrimido[2,1-b]benzazoles
  作者：Ahmad Reza Moosavi-Zare、Hamid Goudarziafshar、Parva Fashi

  DOI：10.1007/s11164-020-04279-5

  日期：2020.12

  was prepared and fully characterized as a new nano-Schiff base complex. Nano-[Co-4CSP]Cl2 was successfully used as an efficient catalyst for the synthesis of some 4H-pyrimido[2,1-b]benzazoles such as 4H-pyrimido[2,1-b]benzothiazoles and 4H-pyrimido[2,1-b]benzimidazoles.

  Nano-Co-[4-clolorophenyl-salsylaldimine-pyranopyrimidine dione]Cl2 Nano-[Co-4CSP]Cl2} 被制备并充分表征为一种新的纳米席夫碱配合物。Nano-[Co-4CSP]Cl2 被成功用作合成一些 4H-嘧啶并[2,1-b]苯并唑类的高效催化剂，例如 4H-嘧啶并[2,1-b]苯并噻唑和 4H-嘧啶并[2 ,1-b]苯并咪唑。
• Green Synthesis of Benzoimidazopyrimidine, Benzimidazoloquinazolinone, Triazolopyrimidine and Triazoloquinazolinone Derivatives Catalyzed by Oxalic Acid Dihydrate
  作者：Seyed Sajad Sajadikhah、Bagher Liravi-Deylami

  DOI：10.2174/1570178618666210506120228

  日期：2022.3

  Benzoimidazopyrimidine, benzimidazoloquinazolinone, triazolopyrimidine, and triazoloquinazolinone derivatives were synthesized via a one-pot multi-component reaction in the presence of a catalytic amount of oxalic acid dihydrate. The reactions were performed in the mixture of EtOH:H2O or under solvent-free conditions as green media. The advantageous features of these methodologies are inexpensive starting materials and catalyst, high atom economy and good yields, and metal-free synthesis. Moreover, all the products were obtained by simple filtration, and no need for column chromatography or tedious separation procedures, which is very important in terms of reducing environmental pollutions.

  摘要：通过一锅多组分反应，在草酸二水合物的催化下合成了苯并咪唑吡啶、苯并咪唑喹唑啉酮、三唑吡嗪和三唑喹唑啉酮衍生物。反应在EtOH:H2O混合物或无溶剂条件下进行，作为绿色介质。这些方法的优点是起始材料和催化剂廉价，原子经济性高，产率良好，且无金属合成。此外，所有产物均通过简单过滤得到，无需柱层析或繁琐的分离程序，这在减少环境污染方面非常重要。
• Shang, Xiaojun; Geng, Mingjiang; Wu, Liqiang, Asian Journal of Chemistry, 2012, vol. 24, # 2, p. 515 - 517
  作者：Shang, Xiaojun、Geng, Mingjiang、Wu, Liqiang

  DOI：——

  日期：——