Lewis acid catalyzed C-3 alkylidenecyclopentenylation of indoles: an easy access to functionalized indoles and bisindoles

被引：7
作者：
Chand, S. Sarath [1 ,2 ]
Sasidhar, B. S. [1 ,2 ]
Prakash, Praveen [2 ]
Sasikumar, P. [2 ]
Preethanuj, P. [2 ]
Jaroschik, Florian [3 ]
Harakat, Dominique [3 ]
Vasse, Jean-Luc [3 ]
Radhakrishnan, K. V. [1 ,2 ]
机构：
[1] Acad Sci & Innovat Res AcSIR, New Delhi 110001, India
[2] CSIR, Organ Chem Sect, Natl Inst Interdisciplinary Sci & Technol, Trivandrum 695019, Kerala, India
[3] Univ Reims, F-51687 Reims 2, France
来源：
RSC ADVANCES | 2015年 / 5卷 / 48期
关键词：
ONE-POT STRATEGY; FRIEDEL-CRAFTS ALKYLATIONS; MESO BICYCLIC HYDRAZINES; STEREOSELECTIVE-SYNTHESIS; DIAZABICYCLIC ALKENES; FACILE ROUTE; ARYL IODIDES; OLEFINS; PENTAFULVENES; CYCLOADDITION;
D O I：
10.1039/c5ra01107h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A Lewis acid catalyzed C-3 alkylidenecylopentenylation of indoles through the ring opening of pentafulvene derived diazabicyclic olefins has been developed. The present protocol offers an efficient route toward the synthesis of indole and bisindole derivatives. The role of the hydrazine group, as a reaction carrier in the strategy has also been demonstrated by the stepwise synthesis of functionalized bisindole.
引用
收藏
页码：38075 / 38084
页数：10
相关论文
共 52 条
  • [1] Catalytic Functionalization of Indoles in a New Dimension
    Bandini, Marco
    Eichholzer, Astrid
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) : 9608 - 9644
  • [2] Organocatalytic strategies for the asymmetric functionalization of indoles
    Bartoli, Giuseppe
    Bencivenni, Giorgio
    Dalpozzo, Renato
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (11) : 4449 - 4465
  • [3] The Expanded Biology of Serotonin
    Berger, Miles
    Gray, John A.
    Roth, Bryan L.
    [J]. ANNUAL REVIEW OF MEDICINE, 2009, 60 : 355 - 366
  • [4] Highly enantioselective Friedel-Crafts alkylations of indoles with simple enones catalyzed by zirconium(IV)-BINOL complexes
    Blay, Gonzalo
    Fernandez, Isabel
    Pedro, Jose R.
    Vila, Carlos
    [J]. ORGANIC LETTERS, 2007, 9 (13) : 2601 - 2604
  • [5] Stereoselective Transformations of meso Bicyclic Hydrazines: Versatile Access to Functionalized Aminocyclopentanes
    Bournaud, Chloee
    Chung, Florence
    Luna, Alejandro Perez
    Pasco, Morgane
    Errasti, Gauthier
    Lecourt, Thomas
    Micouin, Laurent
    [J]. SYNTHESIS-STUTTGART, 2009, (06): : 869 - 887
  • [6] Synthesis and functionalization of Indoles through palladium-catalyzed reactions
    Cacchi, S
    Fabrizi, G
    [J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2873 - 2920
  • [7] Trapping the Lewis acid generated transient species from pentafulvene derived diazanorbornenes with ortho-functionalized aryl iodides and aliphatic alcohols
    Chand, S. Sarath
    Saranya, S.
    Preethanuj, P.
    Dhanya, B. P.
    Jijy, E.
    Prakash, Praveen
    Sasidhar, B. S.
    Szymoniak, Jan
    Santhini, P. V.
    Radhakrishnan, K. V.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (19) : 3045 - 3061
  • [8] Palladium/Lewis Acid Mediated Domino Reaction of Pentafulvene Derived Diazabicyclic Olefins: Efficient Access to Spiropentacyclic Motif with an Indoline and Pyrazolidine Fused to Cyclopentene
    Chand, S. Sarath
    Jijy, E.
    Prakash, Praveen
    Szymoniak, Jan
    Preethanuj, P.
    Dhanya, B. P.
    Radhakrishnan, K. V.
    [J]. ORGANIC LETTERS, 2013, 15 (13) : 3338 - 3341
  • [9] Sequential Copper-Catalyzed Rearrangement-Allylic Substitution of Bicyclic Hydrazines with Grignard Reagents
    Crotti, Stefano
    Bertolini, Ferruccio
    Macchia, Franco
    Pineschi, Mauro
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (06) : 869 - 873
  • [10] Enantioselective indole Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes
    Evans, DA
    Scheidt, KA
    Fandrick, KR
    Lam, HW
    Wu, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) : 10780 - 10781
123456