4-imino-6,7-dimethoxy-3-(4-methoxyphenyl)-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: 4-imino-6,7-dimethoxy-3-(4-methoxyphenyl)-3,4-dihydroquinazoline-2-carbonitrile
• 英文别名: 4-Imino-6,7-dimethoxy-3-(4-methoxyphenyl)quinazoline-2-carbonitrile；4-imino-6,7-dimethoxy-3-(4-methoxyphenyl)quinazoline-2-carbonitrile
• 化学式: C₁₈H₁₆N₄O₃
• 分子量: 336.35
• InChiKey: YTYBYILSNCTXTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (Z)-2-amino-4,5-dimethoxy-N′-(4-methoxyphenyl)benzamidine 、 4,5-二氯-1,2,3-二噻唑氯化物 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61%的产率得到4-imino-6,7-dimethoxy-3-(4-methoxyphenyl)-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

• 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.