2-(3-nitrophenyl)quinazoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(3-nitrophenyl)quinazoline
• 化学式: C₁₄H₉N₃O₂
• 分子量: 251.244
• InChiKey: GDPBFVVLLZTDIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-nitrophenyl)quinazoline 、 2-萘酚 在 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 2-(m-nitrophenyl)-4-(2-hydroxynaphthalen-1-yl)quinazoline
  参考文献：
  名称：

  Metal-free C–H/C–H coupling of 1,3-diazines and 1,2,4-triazines with 2-naphthols facilitated by Brønsted acids

  摘要：

  One-pot protocol metal-free oxidative C-H/C-H coupling of azines with 2-naphthols facilitated by Bronsted acid has been developed. The method affords azinylnaphthols, a basic scaffold of atropisomeric catalysts for asymmetric synthesis and fluorophores. The advantages of the proposed protocol include mild reaction conditions, high regio- and chemoselectivity and also scalability. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131391
• 作为产物：
  描述：

  N-[chloro(3-nitrophenyl)methyl]pyridinium chloride 在 sodium acetate 、 四氯苯醌 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 反应 2.0h， 生成 2-(3-nitrophenyl)quinazoline
  参考文献：
  名称：

  Vanden Eynde; Godin; Mayence, Synthesis, 1993, # 9, p. 867 - 869

  摘要：

  DOI：

文献信息

• A facile and versatile protocol for the one-pot PhI(OAc) 2 mediated divergent synthesis of quinazolines from 2-aminobenzylamine
  作者：Moumita Saha、Prasun Mukherjee、Asish R. Das

  DOI：10.1016/j.tetlet.2017.04.036

  日期：2017.5

  be the key reagent in absence or presence of catalytic amount of molecular iodine (I2)/zinc chloride (ZnCl2) to construct quinazoline scaffold from 2-aminobenzylamine and a variety of easily available aldehydes, aryl and aliphatic amines, aliphatic and aryl alcohols and nitriles. This protocol provides mild and robust conditions along with great versatility to synthesize 2-substituted quinazolines from

  在本工作中，已发现碘代苯二乙酸酯（PIDA）是关键试剂，不存在或存在催化量的分子碘（I 2）/氯化锌（ZnCl 2）来由2-氨基苄胺和多种容易制备的喹唑啉骨架。可用的醛，芳基和脂族胺，脂族和芳基醇和腈。该方案提供了温和而稳定的条件，并具有很好的通用性，可以从多种起始原料以良好至极好的产率合成2-取代的喹唑啉。所开发的方案也非常适用于含有易于氧化的官能团的反应物。
• Niacin as a Potent Organocatalyst towards the Synthesis of Quinazolines Using Nitriles as C-N Source
  作者：Raghuram Gujjarappa、Nagaraju Vodnala、Velma Ganga Reddy、Chandi C. Malakar

  DOI：10.1002/ejoc.201901651

  日期：2020.2.21

  An organocatalyzed protocol has been described for the comprehensive synthesis of 2‐substituted quinazolines using nitriles as C–N source. The developed reaction conditions are suitable for a wide range of substrates providing the desired products in excellent yields.

  已经描述了使用腈作为CN来源全面合成2取代的喹唑啉的有机催化方案。所开发的反应条件适用于各种底物，以优异的产率提供所需的产物。
• Copper-Catalyzed Sequential N-Arylation and Aerobic Oxidation: Synthesis of Quinazoline Derivatives
  作者：Hua Fu、Changmei Cheng、Qing Liu、Yufen Zhao

  DOI：10.1055/s-0033-1339800

  日期：——

  novel and efficient copper-catalyzed cascade method for the synthesis of quinazoline derivatives has been developed. The protocol uses readily available substituted (2-bromophenyl)methylamines and amidine hydrochlorides as the starting materials, inexpensive CuBr as the catalyst, and economical and environment friendly air as the oxidant, and the corresponding quinazoline derivatives were obtained in

  开发了一种新型高效的铜催化级联合成喹唑啉衍生物的方法。该方案以易得的取代（2-溴苯基）甲胺和脒盐酸盐为起始原料，以廉价的CuBr为催化剂，以经济环保的空气为氧化剂，以中等至良好的收率获得了相应的喹唑啉衍生物。该过程经历了连续的分子间 N-芳基化、分子内亲核取代和有氧氧化。
• Copper-catalyzed domino reaction between 1-(2-halophenyl)methanamines and amidines or imidates for the synthesis of 2-substituted quinazolines
  作者：Mohamed A. Omar、Jürgen Conrad、Uwe Beifuss

  DOI：10.1016/j.tet.2014.02.066

  日期：2014.5

  between 1-(2-bromophenyl)methanamines and amidines using K3PO4 as the base, pivalic acid as the additive, and aerial oxygen as the oxidant gives access to substituted quinazolines in a single step with yields in the range between 43 and 90%. It is assumed that the reaction proceeds as a Cu(I)-catalyzed intermolecular N-arylation followed by an intramolecular nucleophilic substitution and a Cu(II)-catalyzed

  以K 3 PO 4为碱，新戊酸为添加剂，空气中的氧气为氧化剂的1-（2-溴苯基）甲胺和am之间的CuI催化的多米诺反应使一步反应可得到取代的喹唑啉范围介于43％和90％之间。假定该反应以Cu（I）催化的分子间N-芳基化进行，然后进行分子内亲核取代和Cu（II）催化的氧化。am可以被酰亚胺取代，反应也可以与1-（2-碘苯基）甲胺一起进行。
• Copper-Catalyzed Synthesis of Quinazolines in Water Starting from o-Bromobenzylbromides and Benzamidines
  作者：Chandi C. Malakar、Alevtina Baskakova、Jürgen Conrad、Uwe Beifuss

  DOI：10.1002/chem.201200583

  日期：2012.7.16

  Water makes it possible: The Cu2O‐catalyzed reaction between easily available o‐bromobenzylbromides and benzamidines by using Cs2CO3 as the base and N,N′‐dimethylethylenediamine (DMEDA) as the additive in water as the solvent gives access to substituted quinazolines in a single step with yields ranging from 57 to 85 % (see scheme).

  水使成为可能：通过使用Cs 2 CO 3作为碱和N，N'-二甲基乙二胺（DMEDA）作为在水中的添加剂作为溶剂，Cu 2 O催化易得的邻溴代溴化苄与苄am之间的反应一步即可取代取代的喹唑啉，产率为57％至85％（请参阅方案）。