3-(4-bromophenyl)-4-imino-3,4-dihydroquinazoline-2-carbonitrile

• 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: 3-(4-bromophenyl)-4-imino-3,4-dihydroquinazoline-2-carbonitrile
• 英文别名: 3-(4-Bromophenyl)-4-iminoquinazoline-2-carbonitrile；3-(4-bromophenyl)-4-iminoquinazoline-2-carbonitrile
• 化学式: C₁₅H₉BrN₄
• 分子量: 325.167
• InChiKey: SQFBYCJZNTZPIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 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：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,5-二氯-1,2,3-二噻唑氯化物 、 2-amino-N′-(4-bromophenyl)benzamidine 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以63%的产率得到3-(4-bromophenyl)-4-imino-3,4-dihydroquinazoline-2-carbonitrile
  参考文献：
  名称：

  One-Step Conversion of 2-Amino-N′-arylbenzamidines into 3-Aryl-4-imino-3,4-dihydroquinazoline-2-carbonitriles Using 4,5-Dichloro-1,2,3-dithiazolium Chloride

  摘要：

  2-Amino-N'-arylbenzamidines react with 4,5-dichloro-1,2,3-dithiazolium chloride (Appel salt) in the presence of Hunig's base (2 equiv) to give in one step 3-aryl-4-imino-3,4-dihydroquinazoline-2-carbonitriles in 53-81% yields. Nine examples are presented along with the single crystal X-ray structure of 4-imino-3-phenyl-3,4-dihydroquinazoline-2-carbonitrile. Furthermore, the behavior of the latter toward both acid and base hydrolysis is investigated. All new compounds are fully characterized, and a mechanistic rationale for the formation of the iminoquinazolines is provided.

  DOI：

  10.1021/jo401648t

文献信息

• The reaction of 2-amino- N ′-arylbenzamidines with tetracyanoethene reinvestigated: routes to imidazoles, quinazolines and quinolino[2′,3′:4,5]imidazo[1,2- c ]quinazoline-8-carbonitrile
  作者：Styliana I. Mirallai、Maria Manoli、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2015.09.049

  日期：2015.11

  with tetracyanoethene (TCNE) to give 2-[2-(2-aminophenyl)-5-imino-1-phenyl-1H-imidazol-4(5H)-ylidene]malononitrile (11a), 4-(phenylamino)quinazoline-2-carbonitrile (5a) and 4-imino-3-phenyl-3,4-dihydroquinazoline-2-carbonitrile (9a). By optimizing the reaction conditions each of the compounds can be isolated as the main product and seven examples of these reactions are described. The [1H-imidazol-4(

  2-氨基- Ñ '-phenylbenzamidine（1A）反应与tetracyanoethene（TCNE），得到2- [2-（2-氨基苯基）-5-亚氨基-1-苯基-1- ħ咪唑-4（5 ħ） -亚基]丙二腈（11A），4-（苯基氨基）喹唑啉-2-甲腈（5A）和4-亚氨基-3-苯基-3,4-二氢喹唑啉-2-甲腈（9A）。通过优化反应条件每种化合物可被分离为主要产物和这些反应的7个例子进行说明。的[1 ħ咪唑-4（5 ħ） -亚基]丙二腈11A也被独立地在三个步骤中合成从2-氨基Ñ' - （2-硝基苯基）苯甲脒（25）和在TCNE 56％的总产率。或者2-氨基苯基或2-硝基苯基-取代的迪姆罗重排[1 ħ咪唑-4（5 ħ） -亚基]丙二腈11A或27与DBU在热DCM，得到2- [2-（2-氨基苯基） -和2- [2-（2-硝基苯基）-5-（苯基亚氨基）-3- ħ咪唑-4（5 ħ） -亚基
• One-Step Conversion of 2-Amino-<i>N</i>′-arylbenzamidines into 3-Aryl-4-imino-3,4-dihydroquinazoline-2-carbonitriles Using 4,5-Dichloro-1,2,3-dithiazolium Chloride
  作者：Styliana I. Mirallai、Manolis J. Manos、Panayiotis A. Koutentis

  DOI：10.1021/jo401648t

  日期：2013.10.4

  2-Amino-N'-arylbenzamidines react with 4,5-dichloro-1,2,3-dithiazolium chloride (Appel salt) in the presence of Hunig's base (2 equiv) to give in one step 3-aryl-4-imino-3,4-dihydroquinazoline-2-carbonitriles in 53-81% yields. Nine examples are presented along with the single crystal X-ray structure of 4-imino-3-phenyl-3,4-dihydroquinazoline-2-carbonitrile. Furthermore, the behavior of the latter toward both acid and base hydrolysis is investigated. All new compounds are fully characterized, and a mechanistic rationale for the formation of the iminoquinazolines is provided.