Inner-outer ring 1,3-bis(trimethylsilyloxy)-1,3-dienes as useful intermediates in the synthesis of helicenes

被引:0
作者
Real, MD [1 ]
Sestelo, JP [1 ]
Sarandeses, LA [1 ]
机构
[1] Univ A Coruna, Dept Quim Fundamental, E-15071 La Coruna, Spain
关键词
3-bis(trimethylsilyloxy)-1,3-dienes; Diels-Alder reactions; helicenes; quinones; sulfoxides;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Functionalized benzo[c]phenanthrenes ([4]helicenes) and [5]helicenes were synthesised in five steps from tetra-hydronaphthalenone and tetrahydrophenanthrenone compounds using a novel synthetic approach based on a Diels-Alder reaction between inner-outer ring 1,3-bis(trimetliylsilyloxy)-1,3-dienes and benzyne or quinones. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9111 / 9114
页数:4
相关论文
共 50 条
  • [21] Palladium-catalysed isomerisation of 2-vinylidenehydrofurans to 1,3-dienes and some aspects of their reactivity
    Ghobsi, Abdelkader
    Hacini, Salih
    Wavrin, Laurence
    Gaudel-Siri, Anouk
    Corberes, Agnes
    Nicolas, Cyril
    Bonne, Damien
    Viala, Jacques
    Rodriguez, Jean
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (26) : 4446 - 4453
  • [22] Cultivating the Passion to Build Heterocycles from 1,2-Diaza-1,3-dienes: the Force of Imagination
    Attanasi, Orazio A.
    De Crescentini, Lucia
    Favi, Gianfranco
    Filippone, Paolino
    Mantellini, Fabio
    Perrulli, Francesca R.
    Santeusanio, Stefania
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (19) : 3109 - 3127
  • [23] Geometrically specific hydrogen transfer in the reaction of terminally alkyl-substituted 1,3-dienes with 1,4-quinones
    Cameron, DW
    Heisey, RM
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2000, 53 (02) : 109 - 121
  • [24] Dehydrogenative Aza-[4+2] Cycloaddition of Amines with 1,3-Dienes via Dual Catalysis
    Chen, Xiaoxiao
    Zhang, Guoxiang
    Zeng, Rong
    ORGANIC LETTERS, 2021, 23 (18) : 7144 - 7149
  • [25] Synthesis of (E,Z)-1-Alkoxy-3-acyloxy-2-methylpenta-1,3-dienes via Danishefsky-Type Dienes or O-Acylation of Enones
    Laclef, Sylvain
    Exner, Claudia J.
    Turks, Maris
    Videtta, Valeria
    Vogel, Pierre
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22) : 8882 - 8885
  • [26] Asymmetric Cascade Assembly of 1,2-Diaza-1,3-dienes and α,β-Unsaturated Aldehydes via Dienamine Activation
    Ran, Guang-Yao
    Gong, Ming
    Yue, Jing-Fei
    Yang, Xing-Xing
    Zhou, Su-Lan
    Du, Wei
    Chen, Ying-Chun
    ORGANIC LETTERS, 2017, 19 (07) : 1874 - 1877
  • [27] An efficient synthetic route to 1,3-bis(arylethynyl)isobenzofuran using alkoxybenzocyclobutenone as a reactive platform
    Asahina, Kenta
    Matsuoka, Suguru
    Nakayama, Ryosuke
    Hamura, Toshiyuki
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (48) : 9773 - 9776
  • [28] [3+3] Cyclizations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes-a new approach to diverse CF3-substituted fluorenes, dibenzofurans, 9,10-dihydrophenanthrenes and 6H-benzo[c]chromenes
    Buettner, Stefan
    Kelzhanova, Nazken K.
    Abilov, Zharylkasyn A.
    Villinger, Alexander
    Langer, Peter
    TETRAHEDRON, 2012, 68 (18) : 3654 - 3668
  • [29] Regioselective Synthesis of 4-(Arylsulfanyl)-2-hydroxyhomophthalates by [4+2] Cycloaddition of 3-(Arylsulfanyl)-1-(trimethylsilyloxy)buta-1,3-dienes with Dimethyl Penta-2,3-dienedioate
    Imran, Muhammad
    Iqbal, Inam
    Fischer, Christine
    Langer, Peter
    HELVETICA CHIMICA ACTA, 2010, 93 (04) : 704 - 710
  • [30] Palladium-Catalyzed Cascade Double CN Bond Activation: A New Strategy for Aminomethylation of 1,3-Dienes with Aminals
    Qiao, Cuifang
    Chen, Anrong
    Gao, Bingjian
    Liu, Yang
    Huang, Hanmin
    CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (10) : 929 - 933