pyrrolo[1,2-c]quinazolin-5(6H)-one | 1352089-91-8

• 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: pyrrolo[1,2-c]quinazolin-5(6H)-one
• 英文别名: 6H-pyrrolo[1,2-c]quinazolin-5-one
• CAS: 1352089-91-8
• 化学式: C₁₁H₈N₂O
• 分子量: 184.197
• InChiKey: ZOMUVSANKHYYIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-[2-N-(Boc)aminophenyl]-1H-pyrrole 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以96%的产率得到pyrrolo[1,2-c]quinazolin-5(6H)-one
  参考文献：
  名称：

  Aminophenylpyrrole Synthesis and Application to Pyrrolo[1,2-c]quinazolinone Synthesis

  摘要：

  Aminophenylpyrroles have been synthesized by a three-step route from methyl N-(Boc)anthranilate (2). Amine protection of commercially available methyl anthranilate (1) gave Boc-protected methyl ester 2, which reacted with vinylmagnesium bromide in the presence of a catalytic amount of copper (I) cyanide to yield 1-[2-N-(Boc)aminophenyl]pent-4-en-1-one (3) in 43% yield. Oxidation of homoallylic ketone 3 using either a mixture of OsO4 center dot NaIO4 and 2,6-lutidine, or PdCl2-CuCl under oxygen atmosphere gave respectively aldehyde 4 and ketone 5. Treatment of 1,4-dicarbonyl compounds 4 and 5 with ammonium formate as well as primary amines under Paal-Knorr conditions afforded a set of eight 2-[2-N-(Boc)aminophenyl]pyrroles 6a-d and 7a-d. In addition, treatment of 2-[2-N-(Boc)aminophenyl]-1H-pyrrole 6a with NaH provided a novel entry to pyrrolo [1,2-c]quinazolin-5(6H)-one 8.

  DOI：

  10.3987/com-13-s(s)73

文献信息

• One-Pot Synthesis of Pyrrolo[1,2-c]quinazolinone Derivatives
  作者：Kata Mlinarić-Majerski、Matija Petrovčić、Marija Alešković

  DOI：10.1055/s-0034-1379183

  日期：——

  A fast and simple one-pot synthesis of pyrrolo[1,2-c]-quinazolinones is reported. The tandem Suzuki coupling of N-Boc-pyrrol-2-yl boronic acid and ortho-substituted aminoaryl halogenides with subsequent cyclization of the third ring yields a variety of pyrroloquinazolinone scaffolds in good to moderate yields. The palladium-catalyzed cross-coupling reaction is applicable to a wide range of substituted

  报道了一种快速简单的吡咯并 [1,2-c]-喹唑啉酮的一锅法合成。N-Boc-吡咯-2-基硼酸和邻位取代的氨基芳基卤化物的串联 Suzuki 偶联以及随后的第三个环的环化以良好到中等的产率产生各种吡咯并喹唑啉酮支架。钯催化的交叉偶联反应适用于广泛的取代氨基芳基卤化物。
• Optimization of the Suzuki coupling reaction in the synthesis of 2-[(2-substituted)phenyl]pyrrole derivatives
  作者：Marija Alešković、Nikola Basarić、Kata Mlinarić-Majerski

  DOI：10.1002/jhet.792

  日期：2011.11

  A facile three‐step synthesis of 2‐(2‐aminophenyl)pyrrole (1) and 2‐[(2‐aminomethyl)phenyl]pyrrole (2) is reported by use of Suzuki coupling of N‐Boc‐pyrrol‐2‐yl boronic acid (3) and o‐substituted aryl halogenides, followed by hydrogenation. The Pd‐catalyzed cross‐coupling reaction is optimized to be applicable to a wide range of substitued aryl halogenides, with electron‐donating and electron‐withdrawing

  据报道，通过N -Boc-吡咯-2-基的Suzuki偶联，可以轻松实现三步合成2-（2-氨基苯基）吡咯（1）和2-[（（2-氨基甲基）苯基]吡咯（2）。硼酸（3）和邻位取代的芳基卤化物，然后氢化。对Pd催化的交叉偶联反应进行了优化，以适用于具有电子给体和吸电子取代基5a，5b，5c，5d，5e，5f，5g的广泛取代的芳基卤化物。此外，邻溴代苯胺和3的Pd催化偶联可用于吡咯并[1,2 - c ]喹唑啉-5（6 H）-一（8）的一步制备。J.杂环化​​学。（2011）。