dipyrido[1,2-a:2',3'-d]imidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: dipyrido[1,2-a:2',3'-d]imidazole
• 英文别名: dipyrido[1,2-a;2',3'-d]imidazole；imidazo[1,2-a:4,5-b']dipyridine；1,6,8-Triazatricyclo[7.4.0.02,7]trideca-2(7),3,5,8,10,12-hexaene
• 化学式: C₁₀H₇N₃
• 分子量: 169.186
• InChiKey: FXZHBPJCHFJXIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 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：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2'-二吡啶胺 在 羟基甲苯磺酰碘苯 作用下， 以 乙腈 为溶剂， 以74%的产率得到dipyrido[1,2-a:2',3'-d]imidazole
  参考文献：
  名称：

  使用高价碘试剂通过分子内氧化CN键形成苯并咪唑融合的杂环

  摘要：

  在温和条件下，使用高价碘试剂通过芳基CH和NH键之间的CN脱氢脱氢反应的直接方法，为合成各种苯并咪唑稠合的杂环提供了一种通用且方便的方法。 高价碘试剂-CN键形成环化-苯并咪唑稠合的杂环-简单合成-温和条件

  DOI：

  10.1055/s-0030-1260192

文献信息

• Synthesis of Benzimidazole-Fused Heterocycles by Intramolecular Oxidative C-N Bond Formation Using Hypervalent Iodine Reagents
  作者：Noriki Kutsumura、Takao Saito、Shinichi Kunimatsu、Kimiko Kagawa、Takashi Otani

  DOI：10.1055/s-0030-1260192

  日期：2011.10

  dehydrogenative C-N coupling between aryl C-H and N-H bonds using a hypervalent iodine reagent under mild conditions offers a versatile and convenient method for synthesizing various benzimidazole-fused heterocycles. hypervalent iodine reagent - C-N bond forming cyclization - benzimidazole-fused heterocycles - straightforward synthesis - mild conditions

  在温和条件下，使用高价碘试剂通过芳基CH和NH键之间的CN脱氢脱氢反应的直接方法，为合成各种苯并咪唑稠合的杂环提供了一种通用且方便的方法。 高价碘试剂-CN键形成环化-苯并咪唑稠合的杂环-简单合成-温和条件
• Orthogonal and Auto-Tandem Catalysis:  Synthesis of Dipyrido[1,2-<i>a</i>:2‘,3‘-<i>d</i>]imidazole and Its Benzo and Aza Analogues via Inter- and Intramolecular C−N Bond Formation
  作者：Kristof T. J. Loones、Bert U. W. Maes、Caroline Meyers、Joke Deruytter

  DOI：10.1021/jo052091u

  日期：2006.1.1

  The synthesis of dipyrido[1,2-a:2‘,3‘-d]imidazole and hitherto unknown benzo and aza analogues is described. These relatively complex polycyclic heterocycles could be smoothly prepared in one step from commercially available building blocks. Mechanistically, the developed procedure involves orthogonal (Pd and Cu catalyst) or auto-tandem (Pd catalyst) catalysis via regioselective inter- and intramolecular

  描述了双吡啶并[1,2- a：2'，3'- d ]咪唑和迄今未知的苯并氮杂类似物的合成。这些相对复杂的多环杂环可以一步一步从市售构件中顺利制备。从机理上讲，开发的方法涉及通过区域选择性分子间和分子内C-N键形成的正交（Pd和Cu催化剂）或自串联（Pd催化剂）催化。
• Aminoimidazo[1,2-a]pyridines: regioselective synthesis of substituted imidazonaphthyridines, azacarbolines and cyclazines
  作者：Jean M Chezal、Emmanuel Moreau、Olivier Chavignon、Vincent Gaumet、Jacques Métin、Yves Blache、Anna Diez、Xavier Fradera、Javier Luque、Jean C Teulade

  DOI：10.1016/s0040-4020(01)01141-3

  日期：2002.1

  In order to study the regioselectivity of thermal cyclocondensation, aminoimidazo [1,2-a]pyridines (AIP) 5a-e were prepared, further converted into iminophosphoranes 7a-e, and ultimately converted regioselectively in angular annulated imidazonaphthyridines (IN) 8a, 10a, 11a, 12a or linear annulated dipyridoimidazole (DPI) 17a. From 2-substituted derivative 23, the peri annulated product 24a was obtained. The starting amines 5a-f reacted with aldehydes to yield regioselectively IN 8a-c, 10a-c, 11a-c, 12a,b, DPI 16a-e, 17a-d and TIBO like structures (+/-)-13 and 24a-c, as proved by X-ray analysis. The 1,2- or 1,4-addition between amines and alpha,beta-unsaturated aldehydes concerning the pyridine and imidazole moieties is discussed in the light of these results. (C) 2002 Published by Elsevier Science Ltd.
• Hypervalent Iodine(III) Promoted Direct Synthesis of Imidazo[1,2-<i>a</i>]pyrimidines
  作者：Guangyin Qian、Bingxin Liu、Qitao Tan、Siwen Zhang、Bin Xu

  DOI：10.1002/ejoc.201402456

  日期：2014.8

  An efficient and mild synthesis of imidazo[1,2-a]pyrimidine derivatives has been developed from readily available pyrimidyl arylamines or enamines through a hypervalent iodine-promoted intramolecular C–H bond cycloamination reaction. This protocol allows for the facile construction of biologically active bicyclic imidazo[1,2-a]pyrimidine skeletons as well as other imidazo[1,2-a]-type fused heterocycles

  已经从容易获得的嘧啶基芳胺或烯胺通过高价碘促进的分子内 C-H 键环胺化反应开发了一种有效且温和的咪唑并 [1,2-a] 嘧啶衍生物合成方法。该协议允许轻松构建具有生物活性的双环咪唑并 [1,2-a] 嘧啶骨架以及其他咪唑并 [1,2-a] 型稠合杂环。