Lewis Acid Catalyzed Three-Component [3+2] Cycloaddition Reaction Using Pentafulvene as 2π Component: An Easy Way to Construct Pentaleno(1,2-b)indoles

被引:8
作者
Santhini, P. V. [1 ,2 ]
Chand, S. Sarath [1 ,2 ]
John, Jubi [1 ,2 ]
Varma, R. Luxmi [1 ,2 ]
Jaroschik, Florian [3 ,4 ]
Radhakrishnan, K. V. [1 ,2 ]
机构
[1] Natl Inst Interdisciplinary Sci & Technol CSIR, Organ Chem Sect, Trivandrum 695019, Kerala, India
[2] Acad Sci & Innovat Res AcSIR, New Delhi 110001, India
[3] Inst Chim Mol Reims, BP 1039, F-51687 Reims, France
[4] Univ Reims, BP 1039, F-51687 Reims, France
关键词
fulvene; indole; cycloaddition; multicomponent reaction; cyclopentaleno indoles; DIELS-ALDER REACTION; INDOLE ALKALOIDS; FACILE SYNTHESIS; MULTICOMPONENT REACTIONS; 3-OXIDOPYRYLIUM BETAINE; ORGANIC-SYNTHESIS; NATURAL-PRODUCTS; FULVENES; ACCESS; CYCLIZATION;
D O I
10.1055/s-0036-1588696
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile route toward the synthesis of pentaleno(1,2-b) in-doles via multicomponent reaction of indole, aldehyde, and pentafulvene is realized. The reaction proceeds through Lewis acid catalyzed [3+2] cycloaddition of in situ generated indolylmethanol and pentafulvene. This methodology provides an easy access to biologically relevant indole derivatives.
引用
收藏
页码:951 / 956
页数:6
相关论文
共 78 条
  • [11] 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
  • [12] STRUCTURE-FUNCTION RELATIONSHIP OF YUEHCHUKENE .2. THE EFFECT OF C-6-INDOLE ROTATION ON ANTIIMPLANTATION ACTIVITY
    CHENG, KF
    WONG, TT
    CHAN, KP
    KONG, YC
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1992, 27 (02) : 121 - 130
  • [13] Multicomponent reactions: advanced tools for sustainable organic synthesis
    Cioc, Razvan C.
    Ruijter, Eelco
    Orru, Romano V. A.
    [J]. GREEN CHEMISTRY, 2014, 16 (06) : 2958 - 2975
  • [14] One-pot biomimetic total synthesis of yuehchukene via the organocatalytic alkylation-cyclization process of a sterically encumbered α-alkyl enal
    Dange, Nitin S.
    Hong, Bor-Cherng
    Lee, Gene-Hsiang
    [J]. RSC ADVANCES, 2014, 4 (104) : 59706 - 59715
  • [15] Synthesis of polysubstituted cyclopenta[b] indoles via relay gold(I)/Bronsted acid catalysis
    Dhiman, Seema
    Ramasastry, S. S. V.
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (03) : 557 - 560
  • [16] [6+4]CYCLOADDITIONS OF DIETHYLAMINOBUTADIENE TO FULVENES - NEW SYNTHESIS OF AZULENES
    DUNN, LC
    CHANG, YM
    HOUK, KN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (22) : 7095 - 7096
  • [17] Pentafulvene for the Synthesis of Complex Natural Products: Total Syntheses of (±)-Pallambins A and B
    Ebner, Christian
    Carreira, Erick M.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (38) : 11227 - 11230
  • [18] Catalytic C-H bond functionalization with palladium(II):: Aerobic oxidative annulations of indoles
    Ferreira, EM
    Stoltz, BM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) : 9578 - 9579
  • [19] Ferrer C., 2013, J AM CHEM SOC, V135, P7851
  • [20] AMINOCYCLOPENTITOLS FROM FULVENES - SYNTHESES OF (+)-TREHAZOLIN AND THE PENTASUBSTITUTED CYCLOPENTANE OF KERUFFARIDE
    GOERING, BK
    LI, J
    GANEM, B
    [J]. TETRAHEDRON LETTERS, 1995, 36 (49) : 8905 - 8908