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
来源：
SYNLETT | 2017年 / 28卷 / 08期
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
  • [61] [6+3] cycloaddition of fulvenes with 3-oxidopyrylium betaine: a novel methodology for the synthesis of fused cyclooctanoid natural products
    Radhakrishnan, KV
    Krishnan, KS
    Bhadbhade, MM
    Bhosekar, GV
    [J]. TETRAHEDRON LETTERS, 2005, 46 (28) : 4785 - 4788
  • [62] Enantiospecific Total Synthesis of the Hapalindoles, Fischerindoles, and Welwitindolinones via a Redox Economic Approach
    Richter, Jeremy M.
    Ishihara, Yoshihiro
    Masuda, Takeshi
    Whitefield, Brandon W.
    Llamas, Tomas
    Pohjakallio, Antti
    Baran, Phil S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (52) : 17938 - 17954
  • [63] Small Heterocycles in Multicomponent Reactions
    Rotstein, Benjamin H.
    Zaretsky, Serge
    Rai, Vishal
    Yudin, Andrei K.
    [J]. CHEMICAL REVIEWS, 2014, 114 (16) : 8323 - 8359
  • [64] Platinum(II)-Catalyzed Generation and [3+2] Cycloaddition Reaction of α,β-Unsaturated Carbene Complex Intermediates for the Preparation of Polycyclic Compounds
    Saito, Kodai
    Sogou, Hideyuki
    Suga, Takuya
    Kusama, Hiroyuki
    Iwasawa, Nobuharu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (04) : 689 - 691
  • [65] Indoles in Multicomponent Processes (MCPs)
    Shiri, Morteza
    [J]. CHEMICAL REVIEWS, 2012, 112 (06) : 3508 - 3549
  • [66] Simple indole alkaloids and those with a non-rearranged monoterpenoid unit
    Somei, M
    Yamada, F
    [J]. NATURAL PRODUCT REPORTS, 2005, 22 (01) : 73 - 103
  • [67] Catalytic Asymmetric Synthesis of Pyrroloindolines via a Rhodium(II)-Catalyzed Annulation of Indoles
    Spangler, Jillian E.
    Davies, Huw M. L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (18) : 6802 - 6805
  • [68] Discovery of a potent and selective prostaglandin D2 receptor antagonist, [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]-acetic acid (MK-0524)
    Sturino, Claudio F.
    O'Neill, Gary
    Lachance, Nicolas
    Boyd, Michael
    Berthelette, Carl
    Labelle, Marc
    Li, Lianhai
    Roy, Bruno
    Scheigetz, John
    Tsou, Nancy
    Aubin, Yves
    Bateman, Kevin P.
    Chauret, Nathalie
    Day, Stephen H.
    Levesque, Jean-Francois
    Seto, Carmai
    Silva, Jose H.
    Trimble, Laird A.
    Carriere, Marie-Claude
    Denis, Danielle
    Greig, Gillian
    Kargman, Stacia
    Lamontagne, Sonia
    Mathieu, Marie-Claude
    Sawyer, Nicole
    Slipetz, Deborah
    Abraham, William M.
    Jones, Tom
    McAuliffe, Malia
    Piechuta, Hana
    Nicoll-Griffith, Deborah A.
    Wang, Zhaoyin
    Zamboni, Robert
    Young, Robert N.
    Metters, Kathleen M.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (04) : 794 - 806
  • [69] Frustrated Lewis pair catalyzed hydrosilylation and hydrosilane mediated hydrogenation of fulvenes
    Tamke, Sergej
    Daniliuc, Constantin-G.
    Paradies, Jan
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (45) : 9139 - 9144
  • [70] Natural Product Synthesis Using Multicomponent Reaction Strategies
    Toure, Barry B.
    Hall, Dennis G.
    [J]. CHEMICAL REVIEWS, 2009, 109 (09) : 4439 - 4486
12345678