Syntheses of Chromenes and Chromanes via o-Quinone Methide Intermediates

被引:136
|
作者
Ferreira, Sabrina B. [1 ]
da Silva, Fernando de C. [1 ,2 ]
Pinto, Angelo C. [2 ]
Gonzaga, Daniel T. G. [1 ]
Ferreira, Vitor F. [1 ]
机构
[1] Univ Fed Fluminense, Dept Quim Organ, Inst Quim, CEG, BR-24020141 Rio De Janeiro, Brazil
[2] Univ Fed Rio de Janeiro, Ilha Fundao, Inst Quim, Ctr Technol, BR-21949900 Rio De Janeiro, Brazil
关键词
DIELS-ALDER REACTIONS; ONE-POT SYNTHESIS; TROPOLONE NATURAL-PRODUCTS; DEHYDRO-ALPHA-LAPACHONE; BETA-LAPACHONE; IN-VITRO; BIOMIMETIC SYNTHESIS; EFFICIENT SYNTHESIS; ANTITUMOR AGENTS; NAPHTHOQUINONE DERIVATIVES;
D O I
10.1002/jhet.232
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This review intends to explore synthetic methodologies for the preparation of 2H-chromenes and their analog chromanes through ortho-quinone methide (o-QM) intermediates associated with inter and intramolecular hetero-Diels-Alder and electrocyclization reactions.
引用
收藏
页码:1080 / 1097
页数:18
相关论文
共 50 条
  • [1] Chemoenzymatic o-Quinone Methide Formation
    Doyon, Tyler J.
    Perkins, Jonathan C.
    Dockrey, Summer A. Baker
    Romero, Evan O.
    Skinner, Kevin C.
    Zimmerman, Paul M.
    Narayan, Alison R. H.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (51) : 20269 - 20277
  • [2] A cascade Claisen rearrangement/o-quinone methide formation/electrocyclization approach to 2H-chromenes
    Song, Liyan
    Huang, Fang
    Guo, Liwen
    Ouyang, Ming-An
    Tong, Rongbiao
    CHEMICAL COMMUNICATIONS, 2017, 53 (44) : 6021 - 6024
  • [3] Mild and Rapid Method for the Generation of ortho-(Naphtho)quinone Methide Intermediates
    Shaikh, Abdul Kadar
    Cobb, Alexander J. A.
    Varvounis, George
    ORGANIC LETTERS, 2012, 14 (02) : 584 - 587
  • [4] Cycloaddition reactions of o-quinone methides with polarized olefins
    Osyanin, Vitaly A.
    Lukashenko, Anton, V
    Osipov, Dmitry, V
    RUSSIAN CHEMICAL REVIEWS, 2021, 90 (03) : 324 - 373
  • [5] An Oxy-Anion Accelerated [1,5]-o-Quinone Methide Shift During the Nucleophilic Epoxidation of Salicylfulvene
    Yang, Mingwei
    Basada, John
    Gronert, Scott
    Erden, Ihsan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (03) : 362 - 366
  • [6] Multicomponent Reactions (MCRs) with o-Quinone Methides
    Martins, Maria Tereza M.
    Dias, Flaviana Rodrigues F.
    de Moraes, Raphael Silva M.
    da Silva, Marcos Felipe, V
    Lucio, Kaio R.
    Goes, Karin D'Oliveira
    do Nascimento, Patrick A.
    da Silva, Andre S. S.
    Ferreira, Vitor F.
    Cunha, Anna C.
    CHEMICAL RECORD, 2022, 22 (03)
  • [7] One step synthesis of 2-alkenylchromanes via inverse electron-demand Hetero-Diels-Alder reaction of o-quinone methide with unactivated dienes
    Liu, Jian
    Wang, Xiaoxiao
    Xu, Lubin
    Hao, Zhihui
    Wang, Liang
    Xiao, Jian
    TETRAHEDRON, 2016, 72 (47) : 7642 - 7649
  • [8] Quinone Methide Generation via Photoinduced Electron Transfer
    Percivalle, Claudia
    La Rosa, Andrea
    Verga, Daniela
    Doria, Filippo
    Mella, Mariella
    Palumbo, Manlio
    Di Antonio, Marco
    Freccero, Mauro
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (09) : 3096 - 3106
  • [9] Enantioselective synthesis of functionalized 2-amino-4H-chromenes via the o-quinone methides generated from 2-(1-tosylalkyl)phenols
    Wu, Bo
    Gao, Xiang
    Yan, Zhong
    Huang, Wen-Xue
    Zhou, Yong-Gui
    TETRAHEDRON LETTERS, 2015, 56 (29) : 4334 - 4338
  • [10] o-Quinone methides in natural product synthesis: an update
    Gao, Li-Na
    Zheng, Kuan
    Chen, Hui-Yu
    Gao, Yu-Ning
    Li, Zhao-Zhao
    He, Chang
    Huang, Sha-Hua
    Hong, Ran
    Bian, Ming
    Liu, Zhen-Jiang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (12) : 2775 - 2792