Synthesis and Diels-Alder reactions of the furo[3,4-b]pyrrole ring system.: A new indole ring synthesis

被引:12
作者
Moskalev, NV [1 ]
Gribble, GW [1 ]
机构
[1] Dartmouth Coll, Dept Chem, Hanover, NH 03755 USA
基金
美国国家卫生研究院;
关键词
furo[3,4-b]pyrrole; Diels Alder reaction; indole ring synthesis;
D O I
10.1016/S0040-4039(01)02068-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The previously unknown furo[3,4-b]pyrrole ring system has been synthesized from the: appropriate pyrrolo hydroxy-ketones by acid-catalyzed cyclodehydration. Diels-Alder reactions of these furo[3,4-b]pyrroles affords a new synthesis of indoles. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:197 / 201
页数:5
相关论文
共 35 条
  • [1] Synthesis and Diels-Alder reactions of pyrrolo[3,4-b]indoles. A synthesis of 4-acetamidocarbazoles and an approach to the antiostatins
    Pelkey, Erin T.
    Jiang, Jun
    Gribble, Gordon W.
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2013, 90 (10) : 1525 - 1536
  • [2] Tandem furo[3,4-b] pyridine formation -: Diels-Alder reaction:: an approach to the synthesis of nitrogen containing heterocyclic analogues of 1-arylnaphthalene lignans
    Jana, Gouranga P.
    Ghorai, Binay K.
    TETRAHEDRON, 2007, 63 (48) : 12015 - 12025
  • [3] A tandem Diels-Alder/Mannich approach to the synthesis of AE and ABE ring analogues of Delphinium alkaloids
    Goodall, Kirsten J.
    Brimble, Margaret A.
    Barker, David
    TETRAHEDRON, 2012, 68 (29) : 5759 - 5778
  • [4] Diels-Alder reactions of 2-and 3-nitroindoles. A simple hydroxycarbazole synthesis
    Kishbaugh, TLS
    Gribble, GW
    TETRAHEDRON LETTERS, 2001, 42 (29) : 4783 - 4785
  • [5] Synthesis of pyrido[2-3-b]indole derivatives via Diels-Alder reactions of 2-and 3-vinylpyrrolo[2,3-b]pyridines
    Joseph, B
    Da Costa, H
    Mérour, JY
    Léonce, S
    TETRAHEDRON, 2000, 56 (20) : 3189 - 3196
  • [6] The Diels-Alder reaction with O-2,3-dimethylene-1,4-naphthoquinone: A useful intermediate for the synthesis of the B ring of anthracyclinones
    Ferreira, VF
    Pinto, AV
    Pinto, MDFR
    Santos, SC
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 1996, 7 (03) : 169 - 172
  • [7] Design and synthesis of fused polycycles via Diels-Alder reaction and ring-rearrangement metathesis as key steps
    Kotha, Sambasivarao
    Ravikumar, Ongolu
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1259 - 1264
  • [8] Design and synthesis of polycyclic sulfones via Diels-Alder reaction and ring-rearrangement metathesis as key steps
    Kotha, Sambasivarao
    Gunta, Rama
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1373 - 1378
  • [9] Generation of 5,6-dimethylene-2(1H)-pyridinones from [3,4-b] sulfolene pyridinones and application in Diels-Alder reactions
    Govaerts, TC
    Vogels, IA
    Compernolle, F
    Hoornaert, GJ
    TETRAHEDRON, 2004, 60 (02) : 429 - 439
  • [10] Synthesis of Tetrahydropyrazolo[4′,3′:5,6]pyrano[3,4-c]quinolones by Domino Knoevenagel/Hetero Diels-Alder Reactions
    Kiamehr, Mostafa
    Mohammadkhani, Leyla
    Khodabakhshi, Mohammad Reza
    Jafari, Behzad
    Langer, Peter
    SYNLETT, 2019, 30 (15) : 1782 - 1786