3-amino-1-(2,3-dimethoxyphenyl)-1H-benzo[a]pyrano[2,3-c]phenazine-2-carbonitrile | 1263278-24-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: 3-amino-1-(2,3-dimethoxyphenyl)-1H-benzo[a]pyrano[2,3-c]phenazine-2-carbonitrile
• 英文别名: 5-Amino-3-(2,3-dimethoxyphenyl)-6-oxa-15,22-diazapentacyclo[12.8.0.02,7.08,13.016,21]docosa-1(22),2(7),4,8,10,12,14,16,18,20-decaene-4-carbonitrile
• CAS: 1263278-24-5
• 化学式: C₂₈H₂₀N₄O₃
• 分子量: 460.492
• InChiKey: VVALHUJQKSCRRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-羟基-1,4-萘醌 在 copper(II) oxide 作用下， 反应 0.21h， 生成 3-amino-1-(2,3-dimethoxyphenyl)-1H-benzo[a]pyrano[2,3-c]phenazine-2-carbonitrile
  参考文献：
  名称：

  Nano copper(II) oxide catalyzed four-component synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine derivatives

  摘要：

  简历 一项高效的一锅法定量制备功能化苯并[a]吡喃[2,3-c]吩嗪衍生物的方法已被开发，该方法通过2-羟基萘-1,4-二酮、邻苯二胺、醛和丙二腈的四组分反应，在纳米CuO催化剂存在下进行。铜(II)氧化物纳米颗粒可以回收并重复使用多次而不损失其活性。

  DOI：

  10.1016/j.crci.2012.09.012

文献信息

• An efficient four-component domino protocol for the rapid and green synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine derivatives using caffeine as a homogeneous catalyst
  作者：Afshin Yazdani Elah Abadi、Malek-Taher Maghsoodlou、Reza Heydari、Razieh Mohebat

  DOI：10.1007/s11164-015-2083-5

  日期：2016.2

  A one-pot, two-step procedure has been used to synthesize functionalized benzo[a]pyrano[2,3-c]phenazine derivatives from a four-component condensation reaction of 2-hydroxynaphthalene-1,4-dione, o-phenylenediamine, aldehydes, and malononitrile in the presence of 1,3,7-trimethylpurine-2,6-dione (caffeine) as an expedient and reusable solid base catalyst. This new procedure has the following advantages: operational simplicity, short reaction times, environmentally friendly, easy work-up, and all the products were obtained in excellent yields.

  一种一步锅、两步法已被用于合成功能化的苯并[a]吡喃[2,3-c]菲啶衍生物，其方法为：在1,3,7-三甲基嘌呤-2,6-二酮（咖啡因）作为方便易回收的固体碱催化剂存在下，通过2-羟基萘-1,4-二酮、邻苯二胺、醛和丙二腈的四组分缩合反应。该新方法具有以下优点：操作简便、反应时间短、环境友好、易于处理，且所得产物均以优异的产率获得。
• Multicomponent Synthesis of Poly-Substituted Benzo[<i>a</i>]pyrano[2,3-<i>c</i>]phenazine Derivatives under Microwave Heating
  作者：Shu-Liang Wang、Fei-Yue Wu、Chuang Cheng、Ge Zhang、Yin-Ping Liu、Bo Jiang、Feng Shi、Shu-Jiang Tu

  DOI：10.1021/co1000376

  日期：2011.3.14

  one-pot two-step tandem synthesis of highly functionalized benzo[a]pyrano[2,3-c]phenazine derivatives via microwave-assisted multicomponent reactions of 2-hydroxynaphthalene-1,4-dione, diamines, aldehydes, and malononitrile is reported. The procedures are facile, avoiding time-consuming and costly syntheses, tedious workup, and purifications of precursors, as well as protection/deprotection of functional

  通过2-羟基萘-1,4-二酮，二胺，醛和丙二腈的微波辅助多组分反应，新的一锅两步串联合成高度官能化的苯并[a]吡喃并[2,3-c]吩嗪衍生物被报道。该过程是容易的，避免了费时且昂贵的合成，繁琐的后处理和前体的纯化以及对官能团的保护/脱保护。该方法有望在生物活性化合物的组合合成中找到应用，因​​为吩嗪和色烯基序具有广泛的生物活性。
• Theophylline as a new and green catalyst for the one-pot synthesis of spiro[benzo[ a ]pyrano[2,3- c ]phenazine] and benzo[ a ]pyrano[2,3- c ]phenazine derivatives under solvent-free conditions
  作者：Afshin Yazdani-Elah-Abadi、Malek-Taher Maghsoodlou、Razieh Mohebat、Reza Heydari

  DOI：10.1016/j.cclet.2016.09.016

  日期：2017.2

  A green, convenient, high yielding and one-pot procedure for the synthesis of novel spiro[benzo[a]pyrano[2,3-c]phenazine] derivatives by domino multi-component condensation reaction between 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamines, ninhydrine, and malononitrile in the presence of a catalytic amount of 1,3-dimethyl-7H-purine-2,6-dione (theophylline) as an expedient, eco-friendly and reusable

  通过2-羟基萘-1,4-之间多米诺骨牌多组分缩合反应合成新型螺[苯并[a]吡喃并[2,3-c]吩嗪]衍生物的绿色简便方法催化量的1,3-二甲基-7H-嘌呤-2,6-二酮（茶碱）的存在下，二酮，苯1,2-二胺，茚三酮和丙二腈作为一种方便，生态友好且可重复使用的固体碱催化剂在热，微波辐射和无溶剂条件下。该方法也已成功用于苯并[a]吡喃并[2,3-c]吩嗪的合成。
• Multisulfonate hyperbranched polyglycerol functionalized graphene oxide as an efficient reusable catalyst for green synthesis of benzo[<i>a</i>]pyrano-[2,3-<i>c</i>]phenazines under solvent-free conditions
  作者：Hossein Naeimi、Maryam Farahnak Zarabi

  DOI：10.1039/c8ra10180a

  日期：——

  displayed a good loading level of acidic groups on the surface because of coating graphene oxide with HPG. This new catalyst is demonstrated to be highly effective in the preparation of benzo[a]pyrano[2,3-c]phenazine dyes.

  基于在氧化石墨烯表面生长超支化聚甘油（HPG）制备了一种新型酸催化剂。然后，氧化石墨烯上 HPG 的羟基被磺酸基官能化，形成酸催化剂。由于用 HPG 涂覆氧化石墨烯，催化剂在表面上显示出良好的酸性基团负载水平。这种新催化剂被证明在苯并[ a ]吡喃[2,3- c ]吩嗪染料的制备中非常有效。
• [(EtO)3Si(CH2)3N+H3][CH3COO−] as Basic Ionic Liquid Catalyst Promoted Green Synthesis of Benzo[a]pyrano[2,3-c]phenazine Derivatives in Homogenous Solution
  作者：Farhad Shirzaei、Hamid Reza Shaterian

  DOI：10.1007/s10953-023-01332-w

  日期：2024.2

  3-c]phenazine derivatives from four-component condensation reaction of 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamine, aromatic aldehydes, and malononitrile in the presence of [(EtO)3Si(CH2)3N+H3][CH3COO−] as basic ionic liquid as catalyst in homogenous solution under solvent-free conditions at 90 °C is described. Simple procedure, high yields, short reaction times, and an environmentally benign method are

  一种高效的一锅定量方法，用于从 2-羟基萘-1,4-二酮、苯-1,2-二胺的四组分缩合反应制备苯并[ a ]吡喃并[2,3-c]吩嗪衍生物、芳香醛和丙二腈，在[(EtO) 3 Si(CH 2 ) 3 N + H 3 ][CH 3 COO - ]作为碱性离子液体作为催化剂的存在下，在无溶剂条件下于90 °C下在均匀溶液中被描述。该方案具有程序简单、产率高、反应时间短和环境友好的优点。[(EtO) 3 Si(CH 2 ) 3 N + H 3 ][CH 3 COO - ]可以回收并重复使用多次而不损失其活性。