5-amino-1,7-dihydro-7-(4-methoxyphenyl)pyrano[3,2-b]pyrrole-6-carbonitrile | 1404048-26-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-amino-1,7-dihydro-7-(4-methoxyphenyl)pyrano[3,2-b]pyrrole-6-carbonitrile
• 英文别名: 5-amino-7-(4-methoxyphenyl)-1,7-dihydropyrano[3,2-b]pyrrole-6-carbonitrile
• CAS: 1404048-26-5
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: ZLFXWXYGPTUCMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  84.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-羟基吡咯 、 4-甲氧基苯甲醛 、 丙二腈 在 ferric hydrogen sulfate 作用下， 以 乙腈 为溶剂， 反应 7.0h， 以73%的产率得到5-amino-1,7-dihydro-7-(4-methoxyphenyl)pyrano[3,2-b]pyrrole-6-carbonitrile
  参考文献：
  名称：

  A novel and facile approach for synthesis of 5-amino-7-aryl-6-cyano-4H-pyrano[3,2-b]pyrroles

  摘要：

  报告了一种高效的铁催化合成 4H-吡喃并[3,2-b]吡咯的方法。以氢硫酸铁（Fe(HSO4)3）为催化剂，通过 3-羟基吡咯、丙二腈和各种醛的单锅三组分环缩合反应，得到 4H-吡喃并[3,2-b]吡咯衍生物，收率中等至良好。

  DOI：

  10.1007/s12039-012-0262-0

文献信息

• Synthesis and <i>in vitro</i> antimicrobial evaluation of 5-amino-7-aryl-6-cyano-4<i>H</i>- pyrano[3,2,<i>b</i>]pyrrole derivatives catalyzed by reusable ZrOCl<sub>2</sub>•8H<sub>2</sub>O
  作者：A. Mohammed Hussain、S. Sheik Mansoor、K. Aswin、K. Logaiya、S. P.N. Sudhan

  DOI：10.4314/bcse.v28i1.11

  日期：——

  An efficient synthesis of a new series of 5-amino-7-aryl-6-cyano-4H-pyrano[3,2-b]pyrrole derivatives from the reaction of 3-hydroxypyrrole, malononitrile, and various aromatic aldehydes using ZrOCl2·8H2O, an environmentally friendly catalyst under a thermal solvent-free green procedure is described. This simple protocol offer advantages such as shorter reaction times, simple work-up and excellent yield. The catalyst ZrOCl2·8H2O can be reused. The reusability of the catalyst has been studied for the synthesis of 5-amino-7-aryl-6-cyano-4H-pyrano[3,2-b]pyrrole. All the compounds were screened for their antibacterial and antifungal activity.

  本研究采用无溶剂热绿色工艺，使用环保催化剂 ZrOCl2-8H2O，从 3-羟基吡咯、丙二腈和各种芳香醛反应中高效合成了一系列新的 5-氨基-7-芳基-6-氰基-4H-吡喃并[3,2-b]吡咯衍生物。这种简单的方法具有反应时间短、操作简单和收率高的优点。催化剂 ZrOCl2-8H2O 可以重复使用。在合成 5-氨基-7-芳基-6-氰基-4H-吡喃并[3,2-b]吡咯时，对催化剂的可重复使用性进行了研究。对所有化合物进行了抗菌和抗真菌活性筛选。
• A novel multicomponent Zr-catalyzed synthesis of functionalized pyrano[3,2-b]pyrrole derivatives
  作者：Saman Damavandi、Reza Sandaroos、Gholam Hossein Zohuri、Saied Ahmadjo

  DOI：10.1007/s11164-012-0965-3

  日期：2014.1

  A novel, efficient, and rapid procedure, one-pot condensation of 3-hydroxypyrrole, malononitrile, and aromatic aldehydes, with 10 mol % bis[N-(3,5-dicumylsalicylidene)anthracylaminato]zirconium(IV) dichloride as catalyst, in the presence of ultrasonic irradiation, has been developed for synthesis of 5-amino-7-aryl-6-cyano-4H-pyrano[3,2-b]pyrrole derivatives.

  一种新颖、高效、快速的方法，即用 10 mol ；%的双[N-(3,5-二金酰基水杨醛)蒽基氨基]二氯化锆作为催化剂，在超声波辐照下合成 5-氨基-7-芳基-6-氰基-4H-吡喃并[3,2-b]吡咯衍生物。
• Facile one-pot synthesis of 5-amino-7-aryl-6-cyano-4H-pyrano[3,2-b]pyrroles using supported hydrogen sulfate ionic liquid
  作者：Reza Sandaroos、Saman Damavandi、Mehri Salimi

  DOI：10.1007/s00706-012-0744-2

  日期：2012.12

  Twelve new derivatives of 5-amino-7-aryl-6-cyano-4H-pyrano[3,2-b]pyrrole were prepared by one-pot acid-catalyzed cyclocondensation reaction of 3-hydroxypyrrole, malononitrile, and various aldehydes in the presence of the silica-supported ionic liquid 1-methyl-3-(triethoxysilylpropyl)imidazolium hydrogen sulfate as catalyst. The reaction efficiencies were enhanced by moderate electron-withdrawing groups, such Cl and Br, on benzaldehyde, but decreased as substituents became more electron-withdrawing. Among the solvents and catalysts screened for the model reaction, acetonitrile and the silica-supported hydrogen sulfate ionic liquid were found to be the best choices.