3-diazo-1-methylquinoline-2,4(1H,3H)-dione | 41878-47-1

• 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: 3-diazo-1-methylquinoline-2,4(1H,3H)-dione
• 英文别名: 3-Diazonio-1-methyl-4-oxoquinolin-2-olate
• CAS: 41878-47-1
• 化学式: C₁₀H₇N₃O₂
• 分子量: 201.184
• InChiKey: BKYOOZWPUZWHRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  3-diazo-1-methylquinoline-2,4(1H,3H)-dione 在 tris(triphenylphosphine)ruthenium(II) chloride 、 草酰溴 作用下， 以 氟苯 为溶剂， 反应 10.0h， 以62%的产率得到3,4-dibromo-1-methylquinolin-2(1H)-one
  参考文献：
  名称：

  钌（II）催化的重氮二羰基化合物制备各种α，β-和β，β-二卤代烯酮的方案

  摘要：

  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

  DOI：

  10.1002/adsc.201400348
• 作为产物：
  描述：

  4-羟基-N-甲基-2-喹啉 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90%的产率得到3-diazo-1-methylquinoline-2,4(1H,3H)-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。
• A ‘sulfonyl-azide-free’ (SAFE) aqueous-phase diazo transfer reaction for parallel and diversity-oriented synthesis
  作者：Dmitry Dar’in、Grigory Kantin、Mikhail Krasavin

  DOI：10.1039/c9cc02042j

  日期：——

  Diazo transfer reactions are notoriously associated with the use of potentially explosive sulfonyl azides. The first ‘sulfonyl-azide-free’ (SAFE) protocol for producing diazo compounds from their active-methylene precursors via the Regitz diazo transfer reaction was developed and has displayed a remarkable substrate scope. It can be applied to generating arrays of diazo compounds for further evolution

  众所周知，重氮转移反应与潜在爆炸性磺酰叠氮化物的使用有关。研发了第一个通过Regitz重氮转移反应从其活性亚甲基前体生产重氮化合物的“无磺酰叠氮”（SAFE）方案，该方案已显示出显着的底物范围。它可用于产生重氮化合物的阵列，以通过组合化学和一系列支架产生的转化进一步进化。
• A convenient and efficient preparation of β-substituted α-haloenones from diazodicarbonyl compounds
  作者：Yong Rok Lee、Bang Sub Cho、Hyuk Jin Kwon

  DOI：10.1016/j.tet.2003.09.087

  日期：2003.11

  Rhodium(II)-catalyzed reactions of cyclic diazodicarbonyl compounds with a variety of halides have been examined. With acid halides, β-acyloxy α-haloenones are produced in good yields. With benzyl halides, β-benzyloxy α-haloenones are obtained in good yields. Reactions with methylene halides yield β-halomethoxy α-haloenones in good yields, whereas reactions with ethyl halides and ethylene dihalides

  已经研究了铑（II）催化的环状重氮二羰基化合物与各种卤化物的反应。用酰基卤可以高收率生产β-酰氧基α-卤代烯酮。使用苄基卤化物，可以良好的产率获得β-苄氧基α-卤代烯酮。与亚甲基卤的反应以良好的产率产生β-卤代甲氧基α-卤代烯酮，而与乙基卤和乙二卤的反应以高产率产生β-羟基α-卤代烯。这些反应提供了有用且快速的进入β-取代的α-卤代烯酮的途径。还已经用卤化pathway描述了形成这些产物的机理途径。
• Ruthenium catalyzes the synthesis of γ-butenolides fused with cyclohexanones
  作者：Raju S. Thombal、Seoung-Tae Kim、Mu-Hyun Baik、Yong Rok Lee

  DOI：10.1039/c9cc00101h

  日期：——

  Ruthenium(II)-catalyzed reactions of cyclic diazodicarbonyl compounds with β-ketoamides for chemo- and stereoselective construction of cyclohexanone-fused γ-butenolides are described. This study represents the first example of the addition of an enol substrate which is formed by the tautomerization of the β-ketoamides to the electrophilic carbene center for unusual cyclization through amide cleavage

  描述了钌（II）催化的环状重氮二羰基化合物与β-酮酰胺的化学和立体选择性构建，环己酮稠合的γ-丁烯内酯。这项研究代表了添加一个烯醇底物的第一个例子，该底物是通过将β-酮酰胺互变异构化到亲电子卡宾中心形成的，以通过酰胺裂解实现异常环化。组合的实验和计算研究揭示了有利于异常环形成反应的机理途径，而不是一般的羰基叶立德中间体参与产物生成的机理。
• 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。