2-amino-4-(pyridine-3-yl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile | 625376-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-amino-4-(pyridine-3-yl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile
• 英文别名: 2-Amino-6-(hydroxymethyl)-8-oxo-4-(3-pyridinyl)-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile；2-amino-6-(hydroxymethyl)-8-oxo-4-pyridin-3-yl-4H-pyrano[3,2-b]pyran-3-carbonitrile
• CAS: 625376-09-2
• 化学式: C₁₅H₁₁N₃O₄
• 分子量: 297.27
• InChiKey: SDGVJEBYEJGBTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 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：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-吡啶甲醛 、 曲酸 、 丙二腈 在 Ca_9.5Mg_0.5(PO₄)5.5(SiO₄)0.5F_1.5 作用下， 以 乙醇 为溶剂， 反应 0.83h， 以85%的产率得到2-amino-4-(pyridine-3-yl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile
  参考文献：
  名称：

  Green synthesis of pyrano [3,2-b]pyran derivatives using nano Si–Mg–fluorapatite catalyst and the evaluation of their antibacterial and antioxidant properties

  摘要：

  In this study, we synthesize 2-amino-4-alkyl/aryl-6-(hydroxymethyl)-8-oxopyrano[3,2-b] pyran-3-carbonitriles derivatives using a multicomponent reaction featuring aromatic or aliphatic aldehydes, kojic acid, and malononitrile catalyzed by nano fluoroapatite doped with Si and Mg (Si-Mg-FA). All reactions were carried out in EtOH as the solvent under reflux and green condition. The process demonstrates various advantages, including high yields, short reaction times, and simple workup. In addition, toxic organic solvent is not used, nor is chromatographic purification of products required. We characterized the synthesized compounds by Fourier transform infrared,(CNMR)-C-13, and(1)HNMR spectroscopies. Additionally, the antibacterial properties of the pyrano[3,2-b]pyran derivatives were evaluated by determining the minimum inhibitory concentration on two gram-positive and gram-negative bacteria using the macro dilution method and compared with Penicillin and Tetracycline at the same conditions. The 2-amino-4-(2,4-dichlorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile and the 2-amino-4-hexyl-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile show the best antibacterial activity with a MIC value of 62.5 mu g/ml againstStaphylococcus aureus(ATCC 25923). Moreover, the antioxidant properties of the pyrano[3,2-b] pyrans derivatives were evaluated. It is notable that pyrano[3,2-b] pyrans derivatives, synthesized with substituent groups on benzaldehyde such as-NO2, -COOCH3, -OMe show the best antioxidant activity measured by DPPH radical-scavenging method.

  DOI：

  10.1007/s00044-020-02598-1

文献信息

• Ultrasound promoted one-pot synthesis of 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile scaffolds in aqueous media: A complementary ‘green chemistry’ tool to organic synthesis
  作者：Sayed Hossein Banitaba、Javad Safari、Shiva Dehghan Khalili

  DOI：10.1016/j.ultsonch.2012.07.007

  日期：2013.1

  A green and simple approach to assembling of 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile scaffolds via three-component reaction of kojic acid, malononitrile, and aromatic aldehydes in aqueous media under ultrasound irradiation is described. The combinatorial synthesis was achieved for this methodology with applying ultrasound irradiation while making use of water as green solvent. In comparison to conventional methods, experimental simplicity, good functional group tolerance, excellent yields, short routine, and selectivity without the need for a transition metal or base catalyst are prominent features of this green procedure. (C) 2012 Elsevier B.V. All rights reserved.