Syntheses of Chromenes and Chromanes via o-Quinone Methide Intermediates

被引：133
|
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
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2009年 / 46卷 / 06期
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] Simultaneous Synthesis of Both Rings of Chromenes via a Benzannulation/o-Quinone Methide Formation/Electrocyclization Cascade
    Majumdar, Nilanjana
    Korthals, Keith A.
    Wulff, William D.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) : 1357 - 1362
  • [2] 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.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (51) : 20269 - 20277
  • [3] STRUCTURE OF O-QUINONE METHIDE TRIMER
    CAVITT, SB
    SARRAFIZADEH, H
    GARDNER, PD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (04): : 1211 - &
  • [4] Intramolecular Condensation via an o-Quinone Methide: Total Synthesis of (±)-Heliol
    Green, Jason C.
    Brown, Eric R.
    Pettus, Thomas R. R.
    [J]. ORGANIC LETTERS, 2012, 14 (12) : 2929 - 2931
  • [5] STRUCTURES OF SUBSTITUTED O-QUINONE METHIDE TRIMERS
    MERIJAN, A
    GARDNER, PD
    SHOULDERS, BA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (08): : 2148 - &
  • [6] A cascade Claisen rearrangement/o-quinone methide formation/electrocyclization approach to 2H-chromenes
    Song, Liyan
    Huang, Fang
    Guo, Liwen
    Ouyang, Ming-An
    Tong, Rongbiao
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (44) : 6021 - 6024
  • [7] Mild and rapid method for the generation of o-quinone methide intermediates.: Synthesis of puupehedione analogues
    Barrero, Alejandro F.
    del Moral, Jose F. Quilez
    Herrador, M. Mar
    Arteaga, Pilar
    Cortes, Manuel
    Benites, Julio
    Rosellon, Antonio
    [J]. TETRAHEDRON, 2006, 62 (25) : 6012 - 6017
  • [8] The synthesis of some chromans via o-quinone-methide intermediates
    Büyükkidan, B
    Bilgiç, S
    Bilgiç, O
    [J]. SYNTHETIC COMMUNICATIONS, 2001, 31 (08) : 1263 - 1270
  • [9] Progress in Synthesis of Axially Chiral Compounds through aza-Vinylidene o-Quinone Methide Intermediates
    Jiang, Quanbin
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (01) : 159 - 172
  • [10] Identification of o-quinone/quinone methide metabolites of quercetin in a cellular in vitro system
    Awad, HM
    Boersma, MG
    Boeren, S
    van der Woude, H
    van Zanden, J
    van Bladeren, PJ
    Vervoort, J
    Rietjens, IMCM
    [J]. FEBS LETTERS, 2002, 520 (1-3) : 30 - 34
12345