2-(4-methoxyphenyl)-6-nitro-4-phenyl-1,2-dihydroquinazoline | 1283751-74-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 2-(4-methoxyphenyl)-6-nitro-4-phenyl-1,2-dihydroquinazoline
• 英文别名: 6-nitro-2-(4-methoxyphenyl)-4-phenyl-1,2-dihydroquinazoline
• CAS: 1283751-74-5
• 化学式: C₂₁H₁₇N₃O₃
• 分子量: 359.384
• InChiKey: SRSVUGDLASBHQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 2-氨基-5-硝基二苯甲酮 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 2.33h， 以82%的产率得到2-(4-methoxyphenyl)-6-nitro-4-phenyl-1,2-dihydroquinazoline
  参考文献：
  名称：

  Catalyst-free, one pot and three-component synthesis of 4′-phenyl-1′H-spiro[indoline-3,2′-quinazolin]-2-ones and 2,4-diphenyl-1,2-dihydroquinazolines

  摘要：

  A simple, green, efficient and three-component procedure has been developed for the synthesis of 4'-pheny1'H-spiro[indoline-3,2'-quinazolin]-2-ones (4a-m and 6a-g) and 2,4-diphenyl-1,2-dihydroquinazolines (8a-I) by the reaction of 2-aminobenzophenones, isatins or aromatic benzaldehydes and ammonium acetate in excellent yields under catalyst-free conditions using ethanol as a solvent. This method provides several advantages such as operational simplicity, higher yields, shorter reaction time and catalyst-free conditions with ethanol as a solvent makes the method eco-friendly as well as economical. All the 4'pheny1'H-spiro[indoline-3,2'-quinazolin]-2-ones were tested for antimicrobial activity against both Gram-positive and Gram-negative bacterial strains including a fungal strain Candida albicans MTCC 3017. Among these, the compounds 4f, 6a, 6c and 6g showed appreciable antibacterial activity with MIC values 7.8 mu g/ml selectively against Gram-positive bacteria, Micrococcus luteus MTCC 2470. On the other hand, compounds 4j, 4m, 6c and 6g showed good activity with MIC values ranging between 3.9 and 7.8 mu g/ml against Gram-negative bacteria, Klebsiella planticota MTCC 530. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.09.125

文献信息

• Microwave-promoted efficient synthesis of dihydroquinazolines
  作者：Rupam Sarma、Dipak Prajapati

  DOI：10.1039/c0gc00838a

  日期：——

  A solvent- and catalyst-free synthesis of dihydroquinazolines is described. 2,4-Disubstituted-1,2-dihydroquinazolines can be readily obtained from 2-aminobenzophenone and aldehydes under microwave irradiation using urea as an environmentally benign source of ammonia, with a small amount of the corresponding quinazolines as the minor product. The reaction is simple, clean and excellent yields are obtained within minutes.

  介绍了一种无溶剂和催化剂合成二氢喹唑啉的方法。在微波辐照下，使用脲作为对环境无害的氨源，可以很容易地从 2-氨基二苯甲酮和醛中获得 2,4-二取代的-1,2-二氢喹唑啉类化合物，并以少量相应的喹唑啉类化合物作为次要产物。该反应简单、清洁，可在几分钟内获得极高的产率。