pyrrolo[1,2-b]isoquinolin-10(5H)-one | 51491-78-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: pyrrolo[1,2-b]isoquinolin-10(5H)-one
• 英文别名: 5H-pyrrolo[1,2-b]isoquinolin-10-one；5H-pyrrolo[1,2-b]isoquinolin-10-one；Pyrrolo<1,2-b>isochinolin-10(5H)-on
• CAS: 51491-78-2
• 化学式: C₁₂H₉NO
• 分子量: 183.21
• InChiKey: WBDUCNFNRFLPLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-碘苄醇 在 氢氧化钾 、 叔丁基锂 、 三溴化磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 正戊烷 为溶剂， 反应 19.0h， 生成 pyrrolo[1,2-b]isoquinolin-10(5H)-one
  参考文献：
  名称：

  An efficient entry to pyrrolo[1,2-b]isoquinolines and related systems through Parham cyclisation

  摘要：

  Aryllithiums generated by lithium-iodine exchange undergo intramolecular cyclisation to give pyrrolo[1,2-b]isoquinolines, in high yields. The best results were obtained when Weinreb or morpholine amides were used as internal electrophiles. The procedure has been extended to the preparation of seven and eight membered rings, opening a route to benzazepine and benzazocine skeletons. (c) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.105

文献信息

• Facile construction of pyrrolo[1,2-b]isoquinolin-10(5H)-ones via a redox-amination–aromatization–Friedel–Crafts acylation cascade reaction and discovery of novel topoisomerase inhibitors
  作者：Shanchao Wu、Na Liu、Guoqiang Dong、Lin Ma、Shengzheng Wang、Wencai Shi、Kun Fang、Shuqiang Chen、Jian Li、Wannian Zhang、Chunquan Sheng、Wei Wang

  DOI：10.1039/c6cc03071h

  日期：——

  An efficient redox-amination-aromatization-Friedel-Crafts acylation cascade process from trans-4-hydroxyproline and 2-formylbenzoic acids has been developed for the synthesis of pyrrolo[1,2-b]isoquinolin-10(5H)-ones. Compound 3h was identified as a new potent dual topoisomerase I/II inhibitor.

  从反式-4-羟基脯氨酸和2-甲酰基苯甲酸开发了一种有效的氧化还原胺化芳构化Friedel-Crafts酰化级联方法，用于合成吡咯并[1,2-b]异喹啉-10（5H）-。化合物3h被鉴定为新型强效双重拓扑异构酶I / II抑制剂。
• Metalation–cyclisation sequence on N-(o-halobenzyl)pyrroles. Synthesis of pyrrolo[1,2-b]isoquinolones
  作者：Ainhoa Ardeo、Esther Lete、Nuria Sotomayor

  DOI：10.1016/s0040-4039(00)00817-0

  日期：2000.7

  Parham-type cyclisation of N-(o-halobenzyl)pyrroles has been investigated. Aryllithiums generated from metalation of N-(o-iodobenzyl)pyrroles undergo intramolecular cyclisation to give pyrrolo[1,2-b]isoquinolinones in moderate to good yields, if the N,N-diethylcarbamoyl group is used as internal electrophile and the aromatic ring is activated.

  已经研究了N-（邻卤代苄基）吡咯的Parham型环化。如果将N，N-二乙基氨基甲酰基用作内部亲电试剂和芳环，则由N-（邻碘苄基）吡咯金属化生成的芳基锂分子内环化，可以中等至良好的产率得到吡咯并[1,2- b ]异喹啉酮被激活。
• Parham-Type Cycliacylation with Weinreb Amides. Application to the Synthesis of Fused Indolizinone Systems
  作者：Javier Ruiz、Nuria Sotomayor、Esther Lete

  DOI：10.1021/ol034194+

  日期：2003.4.1

  [GRAPHIC]Weinreb amides behave as efficient internal electrophiles in Parham-type cycliacylation reactions. Thus, aryl- and heteroaryllithiums generated by lithium-halogen exchange undergo intramolecular cyclization to give fused indolizinone systems as pyrrolo[1,2-b]isoquinolines, thieno[2,3-f]indolizinones, and pyrrolo[1,2-b]acridinones in high yields.
• STEFANCICH G.; ARTICO M.; MASSA S.; VOMERO S., J. HETEROCYCL. CHEM., 1979, 16, NO 7, 1443-1447
  作者：STEFANCICH G.、 ARTICO M.、 MASSA S.、 VOMERO S.

  DOI：——

  日期：——
• An efficient entry to pyrrolo[1,2-b]isoquinolines and related systems through Parham cyclisation
  作者：Javier Ruiz、Ainhoa Ardeo、Roberto Ignacio、Nuria Sotomayor、Esther Lete

  DOI：10.1016/j.tet.2004.10.105

  日期：2005.3

  Aryllithiums generated by lithium-iodine exchange undergo intramolecular cyclisation to give pyrrolo[1,2-b]isoquinolines, in high yields. The best results were obtained when Weinreb or morpholine amides were used as internal electrophiles. The procedure has been extended to the preparation of seven and eight membered rings, opening a route to benzazepine and benzazocine skeletons. (c) 2004 Elsevier Ltd. All rights reserved.