3-phenylimidazo[5,1-a]isoquinoline | 19382-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-phenylimidazo[5,1-a]isoquinoline
• CAS: 19382-37-7
• 化学式: C₁₇H₁₂N₂
• 分子量: 244.296
• InChiKey: FOWPYBODTMDQKK-UHFFFAOYSA-N

物化性质

• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-phenylimidazo[5,1-a]isoquinoline 在 五氯化磷 作用下， 以 三氯氧磷 为溶剂， 反应 1.0h， 以70%的产率得到1-chloro-3-phenylimidazo<5,1-a>isoquinoline
  参考文献：
  名称：

  Benincori, Tiziana; Brenna, Elisabetta; Sannicolo, Franco, Journal of the Chemical Society. Perkin transactions I, 1993, # 6, p. 675 - 680

  摘要：

  DOI：
• 作为产物：
  描述：

  异喹啉-1-羧酸乙酯 在 盐酸 、 五氯化磷 、 sodium 作用下， 反应 4.17h， 生成 3-phenylimidazo[5,1-a]isoquinoline
  参考文献：
  名称：

  Benincori, Tiziana; Brenna, Elisabetta; Sannicolo, Franco, Journal of the Chemical Society. Perkin transactions I, 1993, # 6, p. 675 - 680

  摘要：

  DOI：

文献信息

• Triflic Anhydride Mediated Synthesis of Imidazo[1,5-<i>a</i>]azines
  作者：Guillaume Pelletier、André B. Charette

  DOI：10.1021/ol400870b

  日期：2013.5.3

  Imidazo[1,5-a]azines are synthesized in moderate to excellent yields using a mild cyclodehydration/aromatization reaction triggered by the use of triflic anhydride (Tf2O) and 2-methoxypyridine (2-MeOPyr). Various substitution patterns and functional groups were found to be compatible under the optimized conditions. In addition, a 5-bromo-3-aryl derivative was also shown to be active in a Sonogashira

  使用温和的环脱水/芳香化反应，通过使用三氟甲磺酸酐（Tf 2 O）和2-甲氧基吡啶（2-MeOPyr）引发，可以中等至极好的收率合成咪唑并[1,5- a ]嗪。发现各种取代模式和官能团在优化条件下是相容的。此外，还显示了5-溴-3-芳基衍生物在Sonogashira交叉偶联和直接芳基化反应中具有活性。叔酰胺与底物相容，可合成三氟甲磺酸咪唑并[1,5- a ]吡啶鎓。
• Electrocatalytic Intermolecular C(sp³)–H/N–H Coupling of Methyl <i>N</i>-Heteroaromatics with Amines and Amino Acids: Access to Imidazo-Fused <i>N</i>-Heterocycles
  作者：Peng Qian、Zicong Yan、Zhenghong Zhou、Kangfei Hu、Jiawei Wang、Zhibin Li、Zhenggen Zha、Zhiyong Wang

  DOI：10.1021/acs.orglett.8b02578

  日期：2018.10.19

  An efficient NH4I-mediated intermolecular annulation of methyl N-heteroaromatics with amines/amino acids was developed by virtue of anodic oxidation, providing a variety of functionalized imidazo-fused N-heterocycles with good to excellent yields. The practicality of this protocol was demonstrated by the readily available starting materials, broad substrate scope, water tolerance, scalability, and

  通过阳极氧化，开发了一种有效的NH 4 I介导的甲基N-杂芳族化合物与胺/氨基酸的分子间环化反应，提供了多种具有良好至优异收率的官能化的咪唑并合的N-杂环。该协议的实用性通过容易获得的起始材料，广泛的底物范围，耐水性，可扩展性以及电解产物的多种转化得到证明。
• Iodine mediated nitrosation of imidazo[1,5-a]N-heteroarenes using TBN ( BuONO) reagent
  作者：Mummadi Sandeep、MD. Muzaffar-ur-Rehman、Kapil Chahal、Kallu Rajender Reddy

  DOI：10.1016/j.tetlet.2021.153401

  日期：2021.10

  An iodine mediated regio-selective nitrosation of imidazo[1,5-a]N-heteroarenes is reported using TBN as nitroso source. This method afford synthetically useful and medicinally interesting 3-nitroso imidazo[1,5-a]N-heteroarenes in moderate to good yields with good functional group tolerance. Further, this reaction could applicable on gram-scale level synthesis.

  碘介导的咪唑并[1,5- a ] N-杂芳烃的区域选择性亚硝化反应使用TBN作为亚硝基源。该方法以中等至良好的收率和良好的官能团耐受性提供了合成有用和医学上有趣的 3-亚硝基咪唑并 [1,5- a ] N-杂芳烃。此外，该反应可应用于克级合成。
• Oxidative Copper‐Catalyzed Regioselective Trifluoromethylation of Fused Imidazo[1,5‐ <i>a</i> ]‐ <i>N</i> ‐heteroarenes using Langlois Reagent
  作者：Mummadi Sandeep、Bangarigalla Shantharjun、Geetala Pradeep Kumar、Kallu Rajender Reddy

  DOI：10.1002/ejoc.202001266

  日期：2021.1.15

  A direct and catalytic method for the regioselective introduction of the medicinally interesting −CF3 group into fused imidazo[1,5‐a]‐N‐heteroarenes via an oxidative copper‐catalyzed C−H bond functionalization reaction has been developed. The reaction proceeds at room temperature using the cheap and stable Langlois reagent (NaSO2CF3) as a CF3 source.

  已经开发了一种直接的催化方法，该方法通过氧化铜催化的CH键官能化反应将医学上有趣的-CF 3基团选择性引入稠合的咪唑并[1,5- a ] -N-杂芳烃中。反应使用便宜且稳定的Langlois试剂（NaSO 2 CF 3）作为CF 3源，在室温下进行。
• Natural α-Amino Acids Applied in the Synthesis of Imidazo[1,5-<i>a</i>]N-heterocycles under Mild Conditions
  作者：Qiang Wang、Shuai Zhang、Fengfeng Guo、Baiqun Zhang、Ping Hu、Zhiyong Wang

  DOI：10.1021/jo302299u

  日期：2012.12.21

  A facile iodine-mediated decarboxylative cyclization from alpha-amino acids and N-heterocyclic carbaldehydes was developed. By virtue of this method, a series of imidazo[1,5-a]N-heterocycles can be synthesized efficiently under mild conditions. A tentative reaction mechanism was proposed based on the experimental results and previous reports.