5-methyl-3-phenyl-5H-pyrido[4,3-b]indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-methyl-3-phenyl-5H-pyrido[4,3-b]indole
• 英文别名: 5-Methyl-3-phenyl[5h]pyrido[4,3-b]indole；5-methyl-3-phenylpyrido[4,3-b]indole
• 化学式: C₁₈H₁₄N₂
• 分子量: 258.323
• InChiKey: JGBBDEZJFQYBQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-碘-1-甲基-1H-吲哚 在 吡啶 、 羟胺 、 三氯氧磷 、 三氯化磷 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 6.5h， 生成 5-methyl-3-phenyl-5H-pyrido[4,3-b]indole
  参考文献：
  名称：

  Cyclizaticn of 3-formyl-2-acetylenylindole oximes

  摘要：

  DOI：

  10.1007/bf00948858

文献信息

• Transition-Metal-Free Access to Pyridocarbazoles from 2-Alkynylindole-3-carbaldehydes via Azomethine Ylide
  作者：Shalini Verma、Pawan K. Mishra、Manoj Kumar、Souvik Sur、Akhilesh K. Verma

  DOI：10.1021/acs.joc.8b00980

  日期：2018.6.15

  An efficient approach for the synthesis of functionalized tetrahydro-pyrido/quinolinocarbazoles from 2-alkynylindole-3-carbaldehydes and l-proline utilizing a metal-free decarboxylative cyclization, ring expansion, and ring contraction strategy via the generation of azomethine ylide was developed. The reaction of 2-alkynylindole-3-carbaldehydes with l-thioproline leads to the formation of γ-carbolines

  开发了一种有效的方法，该方法利用无金属的脱羧环化，环的扩展和环的收缩策略，通过偶氮甲meth内酯的生成，由2-炔基吲哚-3-甲醛和1-脯氨酸合成功能化的四氢吡啶基/喹啉咔唑。2-炔基吲哚-3-甲醛与1-硫代脯氨酸的反应导致形成γ-咔啉。借助于这种方便的方法，可以有效地合成多种生物活性的杂环咔唑。
• Palladium meets copper: one-pot tandem synthesis of pyrido fused heterocycles via Sonogashira conjoined electrophilic cyclization
  作者：Sonu Kumar、Rakesh K. Saunthwal、Trapti Aggarwal、Siva K. Reddy Kotla、Akhilesh K. Verma

  DOI：10.1039/c6ob01539e

  日期：——

  An efficient step-economical tandem approach for the direct synthesis of pyrido fused indole, quinoline, benzofuran and benzothiophene derivatives using a bimetallic Pd/Cu catalytic system has been described. The three component reaction of o-halo aldehydes, alkynes and tert-butylamine leads to the synthesis of biologically active polyheterocycles. The present strategy involves the dual role of tert-butylamine

  已经描述了使用双金属Pd / Cu催化体系直接合成吡啶基稠合的吲哚，喹啉，苯并呋喃和苯并噻吩衍生物的有效的步骤经济的串联方法。邻卤代醛，炔烃和叔丁胺的三组分反应导致生物活性多杂环的合成。本策略涉及叔丁胺和铜（I）在Sonogashira偶联中的双重作用，然后通过亚胺形成进行亲电环化。化学方法已通过X射线晶体学研究验证。
• Regio- and Stereoselective Domino Synthesis of Oxazolo Fused Pyridoindoles and Benzofurooxazolo Pyridines from <i>ortho</i>-Alkynylarylaldehydes
  作者：Shilpi Pal、Deepak Choudhary、Mohit Jainth、Sonu Kumar、Rakesh K. Tiwari、Akhilesh K. Verma

  DOI：10.1021/acs.joc.6b02062

  日期：2016.10.7

  groups. The developed chemistry has been successfully extended for the synthesis of a diverse class of γ-carbolines and benzofuro[3,2-c]pyridines using corresponding ester hydrochlorides of serine, threonine, and cystine as a nitrogen source.

  邻炔基醛4a - t和5a - k与（S）-苯基甘醇6a和6a和6b的反应，对环境友好的Au（III）催化的恶唑并稠合的吡啶并吲哚7a - v和苯并呋喃恶唑并吡啶8a - n的区域和立体选择性多米诺合成。据报道，在温和的反应条件下，使用水作为反应介质的（R）-苯基甘氨醇6b。反应是通过6 -endo-dig在更具亲电性的炔基碳上通过选择性的C–N键形成而进行的环化。该反应可耐受多种官能团。使用相应的丝氨酸，苏氨酸和胱氨酸的酯盐酸盐作为氮源，已成功地将开发的化学方法成功地扩展为合成各种类型的γ-咔啉和苯并呋喃[3,2- c ]吡啶。
• Synthesis of β- and γ-carbolines by the palladium/copper-catalyzed coupling and copper-catalyzed or thermal cyclization of terminal acetylenes
  作者：Haiming Zhang、Richard C Larock

  DOI：10.1016/s0040-4039(02)00005-9

  日期：2002.2

  A variety of 3-substituted β- and γ-carbolines have been synthesized from N-substituted 3-iodoindole-2-carboxaldehydes and 2-bromoindole-3-carboxaldehydes, respectively. The coupling of these aldehydes with various terminal acetylenes using cat. PdCl2(PPh3)2/CuI readily affords the corresponding alkynylindole carboxaldehydes, which have subsequently been converted to the corresponding tert-butylimines

  分别由N-取代的3-碘吲哚-2-甲醛和2-溴吲哚-3-甲醛合成了各种3-取代的β-和γ-咔啉。使用Cat将这些醛与各种末端乙炔偶联。PdCl 2（PPh 3）2 / CuI可以轻松提供相应的炔基吲哚甲醛，随后将其转化为相应的叔丁基亚胺，然后通过铜催化或热法将其环化为β-和γ-咔啉。
• Metal-Free Carbonyl-Assisted Regioselective Hydration of Alkynes: An Access to Dicarbonyls
  作者：Shalini Verma、Manoj Kumar、Pawan K. Mishra、Akhilesh K. Verma

  DOI：10.1021/acs.orglett.9b01649

  日期：2019.7.5

  Metal-free regioselective hydration of o-alkynylaldehydes with the assistance of neighboring carbonyl oxygen is disclosed. The developed protocol provides a facile route to synthesize a series of multisubstituted carbonyl containing scaffolds that enable the potential application toward the synthesis of highly diversified 5-azaindoles. gamma-Carbolines and 2,8-diazacarbazoles can also be accessed directly without isolating the dicarbonyl compounds. The developed methodology is operationally simple and environment-friendly, tolerates a wide variety of functional groups, and is applicable toward large scale synthesis.