2,3,6,7-tetrahydro-8-nitro-7-phenylimidazo[1,2-a]pyridin-5(1H)-one | 1450626-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2,3,6,7-tetrahydro-8-nitro-7-phenylimidazo[1,2-a]pyridin-5(1H)-one
• 英文别名: 2,3,6,7-Tetrahydro-8-nitro-7-phenylimidazo[1,2-a]pyridin-5(1H)-one；8-nitro-7-phenyl-2,3,6,7-tetrahydro-1H-imidazo[1,2-a]pyridin-5-one
• CAS: 1450626-82-0
• 化学式: C₁₃H₁₃N₃O₃
• 分子量: 259.265
• InChiKey: UOYIEZJKVJITED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  肉桂酰氯 、 2-(nitromethylene)imidazolidine 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以88%的产率得到2,3,6,7-tetrahydro-8-nitro-7-phenylimidazo[1,2-a]pyridin-5(1H)-one
  参考文献：
  名称：

  Base-promoted new C–C bond formation: an expedient route for the preparation of thiazolo- and imidazolo-pyridinones via Michael addition

  摘要：

  Base-catalyzed one-pot cyclocondensation reactions of acryloyl and cinnamoyl chlorides with beta-nitroenamine derivatives have been performed under mild conditions and target 7-substituted thiazolo-[3,2-alpha] or imidazolo-[1,2-alpha]pyridin-5-one derivatives were prepared successfully in moderate to good yields. The cyclization reactions may proceed via Michael addition followed by iminoketene-amide tautomerization in view of the products formed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.070

文献信息

• An Efficient One-Pot Four-Component Synthesis of Functionalized Imidazo[1,2-<i>a</i>]pyridines
  作者：Siyavash Kazemi Movahed、Minoo Dabiri、Ayoob Bazgir

  DOI：10.1002/hlca.201200231

  日期：2013.3

  An efficient one‐pot four‐component protocol for the synthesis of imidazo[1,2‐a]pyridines was developed by condensing ethane‐1,2‐diamine (2), 1,1‐bis(methylthio)‐2‐nitroethene (1), aldehydes 3, and activated methylene compounds in EtOH under reflux conditions (Tables 1–3). The features of this procedure are operational simplicity, good yields of products, in situ preparation of heterocyclic ketene

  用于合成咪唑并高效的一锅煮四组分协议[1,2一]吡啶通过冷凝乙烷-1,2-二胺（发达2），1,1-双（甲硫基）-2-硝基乙烯（1），乙醛3和活化亚甲基化合物在EtOH中回流条件下（表1-3）。该方法的特点是操作简便，产品收率高，原位制备杂环烯酮缩醛（HKA）和无催化剂条件。
• Simple synthesis of new imidazopyridinone, pyridopyrimidinone, and thiazolopyridinone derivatives and optimization of reaction parameters using response surface methodology
  作者：Fahimeh Sadat Hosseini、Mohammad Bayat

  DOI：10.1039/c9ra06054e

  日期：——

  The reaction between ketene animal/ketene N,S-acetals (derived from diamines/cysteamine hydrochloride and 1,1-bis(methylthio)-2-nitroethene) with aromatic aldehydes, and Meldrum's acid led to the title compounds. The reaction conditions were optimized using response surface methodology (RSM). The two independent variables (temperature and water content of aqueous ethanol), and the responses (yield

  乙烯酮动物/乙烯酮N、S-缩醛（衍生自二胺/半胱胺盐酸盐和 1,1-双（甲硫基）-2-硝基乙烯）与芳香醛和 Meldrum 酸之间的反应产生了标题化合物。使用响应面法 (RSM) 优化反应条件。研究了两个自变量（含水乙醇的温度和含水量）以及响应（产物的产量和反应时间）。选择的每个参数的范围是：T = 25–100 °C 和水 = 0–100%。最佳值为：T= 72 °C 和水 = 33%。这项工作具有显着优势，包括使用绿色溶剂、实验简单、无需催化剂、简单的后处理和纯化过程、中等至良好的收率以及潜在生物活性化合物的制备。
• Base-promoted new C–C bond formation: an expedient route for the preparation of thiazolo- and imidazolo-pyridinones via Michael addition
  作者：Muhammet Yıldırım、Derya Çelikel、Naciye Evis、David W. Knight、Benson M. Kariuki

  DOI：10.1016/j.tet.2014.06.070

  日期：2014.9

  Base-catalyzed one-pot cyclocondensation reactions of acryloyl and cinnamoyl chlorides with beta-nitroenamine derivatives have been performed under mild conditions and target 7-substituted thiazolo-[3,2-alpha] or imidazolo-[1,2-alpha]pyridin-5-one derivatives were prepared successfully in moderate to good yields. The cyclization reactions may proceed via Michael addition followed by iminoketene-amide tautomerization in view of the products formed. (C) 2014 Elsevier Ltd. All rights reserved.