1-benzyl-3-diazoquinoline-2,4-dione | 223668-13-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-benzyl-3-diazoquinoline-2,4-dione
• 英文别名: 1-Benzyl-3-diazonio-4-oxoquinolin-2-olate
• CAS: 223668-13-1
• 化学式: C₁₆H₁₁N₃O₂
• 分子量: 277.282
• InChiKey: ZESIESXJGNDFTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  71.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-diazoquinoline-2,4-dione 在 dirhodium tetraacetate 作用下， 以 乙腈 为溶剂， 以70%的产率得到1-苄基-3H-吲哚-2-酮
  参考文献：
  名称：

  Efficient synthesis of oxindoles by thermal and rhodium(II)-catalyzed Wolff rearrangement

  摘要：

  An efficient synthesis of oxindoles is achieved from a thermal and rhodium(II)-catalyzed Wolff rearrangement of diazoquinolinediones in moderate yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01714-1
• 作为产物：
  描述：

  1-苄基-4-羟基喹啉-2-酮 在 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以63%的产率得到1-benzyl-3-diazoquinoline-2,4-dione
  参考文献：
  名称：

  Rhodium-Mediated Dipolar Cycloaddition of Diazoquinolinediones

  摘要：

  As an entry to furoquinoline structures of natural origin, the rhodium-mediated dipolar cycloaddition of diazoquinolinediones with alkenes and alkynes has been examined. Because of the unsymmetrical nature of the diazo compounds, both linear and angular furoquinoline products are possible. For the most part, a mixture of regioisomers is generated in moderate to good yields, though in a few cases dominant products are obtained in high yields. The products can be further converted to naturally occurring alkaloids such as isodictamnine. A novel observation in this work is that catalytic quantities of acid enhance the yield and regiochemical control in the cycloaddition.

  DOI：

  10.1021/jo982503h

文献信息

• Synthesis of diverse isatins via ring contraction of 3-diazoquinoline-2,4-diones
  作者：Rajeev Shrestha、Gun Joon Lee、Yong Rok Lee

  DOI：10.1039/c6ra13585d

  日期：——

  An efficient synthesis of diverse isatin derivatives was accomplished by a copper-mediated reaction of 3-diazoquinoline-2,4-diones via ring contraction through domino Wolff rearrangement, decarboxylation, bromination, substitution, and dehydration. This protocol has several advantages as a one-pot procedure, with functional group tolerance, and high yield.

  通过铜介导的多米诺夫·沃尔夫重排，脱羧，溴化，取代和脱水，通过环介导的3-重氮喹啉-2,4-二酮的铜介导反应，完成了各种靛红衍生物的有效合成。该协议作为一锅法具有几个优点，具有官能团耐受性和高收率。
• One-pot construction of diverse and functionalized isochromenoquinolinediones by Rh(<scp>iii</scp>)-catalyzed annulation of unprotected arylamides with 3-diazoquinolinediones and their application for fluorescence sensor
  作者：Rajeev Shrestha、Hari Datta Khanal、Yong Rok Lee

  DOI：10.1039/c9ra03146d

  日期：——

  efficient Rh(III)-catalyzed annulation of arylamides with 3-diazoquinolinediones for the construction of diverse and highly functionalized isochromenoquinolinediones is described. Furthermore, the methodology is applicable for delivering various relevant molecules such as pyridopyranoquinolindiones, thienopyranoquinolinones, and indolopyranoquinolinone. The reaction proceeds via cascade C–H activation, carbene

  描述了一种简便高效的 Rh( III ) 催化芳基酰胺与 3-重氮喹啉二酮的环化，用于构建多种高度功能化的异色烯喹啉二酮。此外，该方法适用于传递各种相关分子，如吡喃并吡喃喹啉二酮、噻吩并吡喃喹啉酮和吲哚吡喃喹啉酮。该反应通过级联 C-H 活化、卡宾插入和分子内内酯化进行。该反应具有高原子经济性、良好的官能团耐受性和高区域选择性。合成的化合物还可以作为 Fe 3+离子的有效荧光传感器。
• Rhodium(III)‐Catalyzed Regioselective C−H Activation/Annulation for the Diverse Pyrazole‐Core Substituted Furans
  作者：Hongyun Cai、Raju S. Thombal、Xin Li、Yong Rok Lee

  DOI：10.1002/adsc.201900498

  日期：2019.9.3

  method for polyfunctionalized furans involving rhodium(III)‐catalyzed pyrazole‐ or indazole‐directed dual C−H functionalization with diazodicarbonyls has been developed. This strategy provides rapid access to diverse tetrasubstituted furans bearing various pyrazoles or indazoles. This unprecedented one‐pot protocol proceeds via cascade C−H activation, metal‐carbene formation, migratory insertion, intramolecular

  已开发出一种新颖且简便的区域选择性合成方法，用于多官能化呋喃，包括铑（III）催化的吡唑或吲唑定向的重氮与双偶氮二羰基双官能化。该策略提供了快速接触带有各种吡唑或吲唑的各种四取代呋喃的途径。这一前所未有的单锅方案通过级联的CH活化，金属碳烯的形成，迁移插入，分子内环化和去质子化而进行。
• Ruthenium(II)-Catalyzed Protocol for Preparation of Diverse α,β- and β,β-Dihaloenones from Diazodicarbonyls
  作者：Krishna Bahadur Somai Magar、Yong Rok Lee

  DOI：10.1002/adsc.201400348

  日期：2014.11.3

  AbstractEfficient one‐step syntheses of α,β‐ and β,β‐dihaloenones were achieved by ruthenium(II)‐catalyzed reactions between cyclic or acyclic diazodicarbonyl compounds and oxalyl chloride or oxalyl bromide in moderate to good yields. This methodology offers several significant advantages, which include ease of handling, mild reaction conditions, one‐step reaction, and the use of an effective and non‐toxic catalyst. The synthesized compounds were further transformed into highly functionalized novel molecules bearing aromatic rings on the enone moiety using the Suzuki reaction.magnified image
• Rhodium-Mediated Dipolar Cycloaddition of Diazoquinolinediones
  作者：Michael C. Pirrung、Florian Blume

  DOI：10.1021/jo982503h

  日期：1999.5.1

  As an entry to furoquinoline structures of natural origin, the rhodium-mediated dipolar cycloaddition of diazoquinolinediones with alkenes and alkynes has been examined. Because of the unsymmetrical nature of the diazo compounds, both linear and angular furoquinoline products are possible. For the most part, a mixture of regioisomers is generated in moderate to good yields, though in a few cases dominant products are obtained in high yields. The products can be further converted to naturally occurring alkaloids such as isodictamnine. A novel observation in this work is that catalytic quantities of acid enhance the yield and regiochemical control in the cycloaddition.