2,3-bis(4-methoxyphenyl)pyrido[2,3-b]pyrazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶吡嗪类
• 英文名称: 2,3-bis(4-methoxyphenyl)pyrido[2,3-b]pyrazine
• 英文别名: 2,3-Bis(4-methoxyphenyl)-pyrido[2,3-b]pyrazine
• 化学式: C₂₁H₁₇N₃O₂
• 分子量: 343.385
• InChiKey: NKNQFYFQAOZSCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  五羰基溴铼(I) 、 2,3-bis(4-methoxyphenyl)pyrido[2,3-b]pyrazine 以 甲苯 为溶剂， 以68%的产率得到fac-[Re(CO)3Br(NC5H3(NC(C6H4OMe)C(C6H4OMe)N))]
  参考文献：
  名称：

  The Re(I) coordination chemistry of a series of pyrido[2,3-b]pyrazine-derived ligands: Syntheses, characterisation and crystal structures

  摘要：

  Reaction of 2,3-diaminopyridine with one equivalent of a functionalised vicinal diketone, in ethanol, yields a series of ligands based upon the pyrido[2,3-b]pyrazine core. The ligands were characterised by (1)H, (13)C-{(1)H} NMR, MS and UV-Vis spectroscopy. Reaction of the ligands with one equivalent of (ReBr(CO)(5)) gave a series of Re-L(n) complexes based upon the general formula fac-[ReBr(CO)(3)(L)] (where L = pyrido[2,3-b]pyrazine-derived ligands, L(1)-L(6)). Solution IR studies confirmed the retention of the facially capped, tri-carbonyl coordination geometry at rhenium, and (1)H NMR studies confirmed coordination of the ligand to Re(I). El HR MS data were obtained for each complex confirming the proposed formulation and stoichiometry. Single crystal X-ray structures were obtained for three of the complexes (Re-L(1), Re-L(2), Re-L(6)), with each demonstrating that the ligands coordinate to Re([) in a bidentate manner, via a four-membered chelate ring, which was unsymmetrical in the former two cases. The electronic absorption spectra of the complexes showed absorption into the visible region ca. 375-500 nm, (the complexes are orange-red in appearance). Following irradiation at 350-450 nm, the complexes display a solid-state broad emission peaking between 600-700 nm. The complexes were not sufficiently luminescent in solution to allow further investigation into the origin of this emission band, although with reference to related 1,8-naphthyridine complexes of Re(I) it is likely to incorporate significant (3)MLCT character. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2009.11.013
• 作为产物：
  描述：

  2,3-二氨基吡啶 、 二氢茴香偶姻 在 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 40.0h， 以87%的产率得到2,3-bis(4-methoxyphenyl)pyrido[2,3-b]pyrazine
  参考文献：
  名称：

  碳纳米管-金纳米杂化邻位二醇和酮醇与二胺的级联反应合成喹喔啉

  摘要：

  据报道，采用金-碳纳米管纳米杂化物作为非均相催化剂，由一氧化碳-缩合法可以容易地从易得的苯偶姻或苯甲醇和1,2-苯二胺或2,3-二氨基吡啶合成喹喔啉。喹喔啉是在温和的条件下在空气中以高收率形成的。简单有效的方法为传统的酸和/或碱催化热工艺提供了一种安全，可持续的替代方法。

  DOI：

  10.1002/cctc.201402782

文献信息

• A general and inexpensive protocol for the nanomagnetic 5-sulfosalicylic acid catalyzed the synthesis of tetrahydrobenzo[b]pyrans and quinoxaline derivatives
  作者：Farzaneh Saboury、Najmedin Azizi、Zohreh Mirjafari、Mohammad Mahmoudi Hashemi

  DOI：10.1007/s13738-020-01948-5

  日期：2020.10

  Fe3O4@SiO2@5-SA (20 mg) showed excellent reactivity for greener synthesis of tetrahydrobenzo[b]pyrans via a three-component reaction of different aromatic aldehydes, malononitrile and dimedone in good to excellent yields (70–95%) in pure water at short reaction times (40–150 min). The method shows eco-friendly synthesis of quinoxaline derivatives from direct condensation of substituted 1,2-diamine with various

  在这项研究中，通过将水溶性5-磺基水杨酸锚定在表面二氧化硅改性的Fe 3 O 4上，制备了具有高负载多功能酸性基团的新型酸官能化磁性纳米粒子。磁性可循环利用的Fe 3 O 4 @SiO 2@ 5-SA（20毫克）显示出不同的芳香性醛，丙二腈和二甲酮的三组分反应，可在较短的时间里纯净水中获得良好至优异的收率（70-95％），从而对绿色四氢苯并[b]吡喃的合成具有优异的反应性。反应时间（40–150分钟）。该方法表明，在室温下，乙醇中的取代的1,2-二胺与各种1,2-二羰基直接缩合，可以生态友好地合成喹喔啉衍生物，从而在较短的时间内即可获得所需的喹喔啉，并具有良好或优异的收率（60-97％）反应时间（120–240分钟）。用扫描电子显微镜，X射线粉末衍射，傅立叶平移红外光谱，振动样品磁强计和热重分析法研究了MNP的形态和磁性。结果表明，Fe 3 O4 @SiO 2 @ 5-SA催化剂可通过外部
• Catalytic application of recyclable silica-supported bismuth(III) chloride in the benzo[N,N]-heterocyclic condensation
  作者：Kioumars Aghapoor、Farshid Mohsenzadeh、Atena Shakeri、Hossein Reza Darabi、Mitra Ghassemzadeh、Bernhard Neumüller

  DOI：10.1016/j.jorganchem.2013.06.037

  日期：2013.10

  Silica-supported bismuth(III) chloride (BiCl3/SiO2) has been successfully employed in the condensation of 1,2-dicarbonyls with a variety of arene-1,2-diamines bearing either electron withdrawing or donating functional groups. The catalyzed reaction proceeded smoothly under ambient temperature in methanol to give the corresponding quinoxaline and pyrido[2,3-b]pyrazine compounds in good to excellent

  二氧化硅负载的氯化铋（III）（BiCl 3 / SiO 2）已成功地用于1,2-二羰基化合物与各种带有吸电子或供电子官能团的芳烃1,2-二胺的缩合反应。催化的反应在环境温度下在甲醇中平稳进行，以良好的至优异的产率得到相应的喹喔啉和吡啶并[2,3- b ]吡嗪化合物。与均相BiCl 3相比，该催化剂具有显着的可重用活性和更高的催化性能。介绍了一种可行的BiCl 3 / SiO 2催化作用机理。此外，制备的不对称苯并[ N]的晶体结构，Ñ ] -heterocycles已经通过单晶X射线衍射来确定。
• Heterogeneous SnCl₂/SiO₂versus Homogeneous SnCl₂Acid Catalysis in the Benzo[N,N]-heterocyclic Condensation
  作者：Hossein Reza Darabi、Kioumars Aghapoor、Farshid Mohsenzadeh、Mohammad Reza Jalali、Shiva Talebian、Leila Ebadi-Nia、Ehsan Khatamifar、Ali Aghaee

  DOI：10.5012/bkcs.2011.32.1.213

  日期：2011.1.20

  The scope of homogeneous Lewis acid-catalyzed benzo[N,N]-heterocyclic condensation was expanded to include the use of various metal salts not reported in the literature and $SnCl_2\cdot}2H_2O$ was finally selected. Among various solid supports activated with $SnCl_2$, heterogeneous $SnCl_2/SiO_2$ proved to be the most effective and significantly higher conversions were achieved compared to $SnCl_2\cdot}2H_2O$ itself. The results of TG-DTA and BET indicated that dispersed $SnCl_2$ coordinates with surface hydroxyl groups of silica leading to formation of stable Lewis acid sites. Low catalyst loading, operational simplicity, practicability and applicability to various substrates render this eco-friendly approach as an interesting alternative to previously applied procedures.

  均质路易斯酸催化的苯并[N,N]-杂环缩合反应的范围扩大到包括使用各种文献中未报道的金属盐，最终选择了$SnCl_2\cdot}2H_2O$。在各种用$SnCl_2$活化的固体载体中，非均质$SnCl_2/SiO_2$被证明是最有效的，相比于$SnCl_2\cdot}2H_2O$自身实现了显著更高的转化率。TG-DTA和BET的结果表明，分散的$SnCl_2$与硅氧化物表面的羟基配位，导致形成稳定的路易斯酸位点。低催化剂负载、操作简单、实用性强以及适用于多种底物使得这种环保的方法成为以前应用程序的有趣替代方案。
• Zirconium Schiff-Base Complex Modified Mesoporous Silica as an Efficient Catalyst for the Synthesis of Nitrogen Containing Pyrazine Based Heterocycles
  作者：Reihaneh Malakooti、Ghasem Rezanejade Bardajee、Hesamaldin Mahmoudi、Nahale Kakavand

  DOI：10.1007/s10562-013-0999-1

  日期：2013.8

  Zirconium Schiff-base complex modified SBA-15 was synthesized and characterized by powder X-ray diffraction (XRD), BET nitrogen adsorption–desorption methods, IR spectroscopy and thermogravimetric analysis. The XRD and BET analyses show that textural properties of SBA-15 were retained during the grafting procedure. The modified SBA was successfully applied as a heterogeneous catalyst for the synthesis

  合成了锆席夫碱配合物改性的 SBA-15，并通过粉末 X 射线衍射 (XRD)、BET 氮吸附-解吸方法、红外光谱和热重分析进行了表征。XRD 和 BET 分析表明 SBA-15 的结构特性在接枝过程中得以保留。改性的 SBA 作为多相催化剂成功应用于合成含氮吡嗪基杂环库，在水介质中以良好的收率。图文摘要锆席夫碱配合物改性介孔二氧化硅作为合成含氮杂环的有效催化剂吡嗪基杂环
• Sustainable approach to tandem catalysis: Expedient access to quinoxalines and pyrido[2,3-b]pyrazines from α-hydroxyketones via microwave-induced [(NH4)6Mo7O24·4H2O – PEG 300] polar paste catalyst system
  作者：Kioumars Aghapoor、Farshid Mohsenzadeh、Mina Mohebi Morad、Hossein Reza Darabi

  DOI：10.1016/j.crci.2012.06.007

  日期：2012.9

  Résumé [(NH4)6Mo7O24·4H2O–PEG 300] is introduced as a polar paste catalyst system for tandem synthesis of quinoxalines and pyrido[2,3-b]pyrazines under open-vessel focused microwave irradiation. Low conversions were obtained when catalyst or PEG was used individually. Accordingly, a convenient combination of catalyst and PEG mostly led to quantitative yield of products within 15 min microwave irradiation with good turnover frequency values (11–20 h−1) taking a tandem process into consideration. The salient features of this environmentally benign method are fast conversions, high product selectivity and the use of a low-cost, readily available, nontoxic, catalyst and medium.

  摘要 [(NH4)6Mo7O24·4H2O–PEG 300] 被引入作为极性浆状催化剂系统，用于在开放容器中进行聚焦微波辐射下的喹啉类化合物和吡啶[2,3-b]吡唑的串联合成。当单独使用催化剂或PEG时，转化率较低。因此，将催化剂和PEG方便地结合在一起，通常在15分钟的微波辐射内实现定量产率，并考虑到串联过程时具有良好的周转频率值（11–20 h−1）。该环保友好方法的显著特点是快速转化、高产物选择性，以及使用低成本、易获取、无毒的催化剂和介质。