4-amino-3-phenylquinazolin-2-one | 67461-76-1

• 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-amino-3-phenylquinazolin-2-one
• 英文别名: 4-imino-3-phenyl-1,2,3,4-tetrahydroquinazolin-2-one；2-oxo-3-phenyl-4-imino-1,2,3,4-tetrahydroquinazoline；4-imino-3-phenyl-3,4-dihydroquinazolin-2(1H)-one；2-Oxo-4-imino-3-phenyl-1,2,3,4-tetrahydro-chinazolin；3-Phenyl-4-imino-1,2,3,4-tetrahydro-chinazolon-(2)；4-imino-3-phenyl-3,4-dihydro-1H-quinazolin-2-one
• CAS: 67461-76-1
• 化学式: C₁₄H₁₁N₃O
• 分子量: 237.261
• InChiKey: VKUNUGUCCKLUFO-UHFFFAOYSA-N

物化性质

• 熔点：
  224 °C
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.64
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-amino-3-phenylquinazolin-2-one 在 sodium hydroxide 作用下， 反应 168.0h， 以90%的产率得到3-苯基-2,4(1H,3H)-喹唑啉二酮
  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
• 作为产物：
  描述：

  1-(2-氰基苯基)-3-苯基脲 在 sodium acetate 、 溶剂黄146 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 4-amino-3-phenylquinazolin-2-one
  参考文献：
  名称：

  Substituent effects on the rate of cyclization of N-phenyl-N?-(o-cyanophenyl)urea in solution

  摘要：

  DOI：

  10.1007/bf00956118

文献信息

• Synthesis and X-ray characterisation of a new polycondensed heterocycle obtained by a novel Mn(III)-mediated cascade reaction of 2-cyanophenyl isothiocyanate
  作者：Gianluca Calestani、Laura Capella、Rino Leardini、Matteo Minozzi、Daniele Nanni、Romina Papa、Giuseppe Zanardi

  DOI：10.1016/s0040-4020(01)00678-0

  日期：2001.8

  loss of a CS moiety. The yields were close to 90% when the reaction was carried out in the presence of diethyl malonate. This compound was unambiguously identified by X-ray crystallography. Under the same conditions, 2-(methoxycarbonyl)phenyl isothiocyanate gave a quinazolinimine derivative instead which is likely to arise from cyclisation of an intermediate N,N′-diarylthiourea. The mechanism of formation

  2-氰基苯基异硫氰酸酯与乙酸锰（III）在乙酸或乙腈中反应，可得到新的缩聚杂环化合物，得益于两个起始异硫氰酸酯分子的结合而失去了CS部分，从而得到了新的缩合杂环。当反应在丙二酸二乙酯存在下进行时，收率接近90％。通过X射线晶体学清楚地鉴定出该化合物。在相同条件下，2-（甲氧基羰基）苯基异硫氰酸酯代替了喹唑啉亚胺衍生物，该衍生物可能是由中间体N，N'-二芳基硫脲的环化产生的。前一种化合物的形成机理可能涉及N，N的形成′-双（2-氰基苯基）硫脲，然后进行相应的环状亚胺衍生物的重排和自由基串联闭环。半假设计算也支持该假设。
• Substituent effects on the rate of cyclization of N-phenyl-N?-(o-cyanophenyl)urea in solution
  作者：I. V. Vasil'eva、�. N. Teleshov、A. N. Pravednikov

  DOI：10.1007/bf00956118

  日期：1985.6
• 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.