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
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
下载
收藏
页码:1080 / 1097
页数:18
相关论文
共 50 条
  • [21] o-quinone methides:: intermediates underdeveloped and underutilized in organic synthesis
    Van de Water, RW
    Pettus, TRR
    TETRAHEDRON, 2002, 58 (27) : 5367 - 5405
  • [22] Intramolecular [4+2] cycloaddition of a photogenerated o-quinone methide in aqueous solution
    Department of Chemistry, Box 3065, University of Victoria, Victoria, BC V8W 3V6, Canada
    J. Photochem. Photobiol. A Chem., 1-3 (91-96):
  • [23] Alkylation of amino acids and glutathione in water by o-quinone methide.: Reactivity and selectivity
    Modica, E
    Zanaletti, R
    Freccero, M
    Mella, M
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01): : 41 - 52
  • [24] Studies toward the Total Synthesis of Parvifolals A/B: An Intramolecular o-Quinone Methide [4
    Paymode, Dinesh J.
    Ramana, Chepuri V.
    ACS OMEGA, 2019, 4 (01): : 810 - 818
  • [25] Intramolecular [4+2] cycloaddition of a photogenerated o-quinone methide in aqueous solution
    Barker, B
    Diao, L
    Wan, P
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1997, 104 (1-3) : 91 - 96
  • [26] o-Quinone Methides and o-Quinone Sulfides via Arynes: Synthesis of Ortho-Disubstituted Arenes and Heterocycles
    Sharma, Abhilash
    Hazarika, Hemanta
    Gogoi, Pranjal
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (07): : 4883 - 4895
  • [27] STEREOSELECTIVE BENZYLIC DEPROTONATION IN THE ENZYMATIC REARRANGEMENT OF N-ACETYLDOPAMINE DERIVED O-QUINONE TO THE P-QUINONE METHIDE
    PETER, MG
    MERZ, A
    TETRAHEDRON-ASYMMETRY, 1995, 6 (04) : 839 - 842
  • [28] Utilizing o-quinone methide chemistry: synthesis of sterically hindered acridin-4-ols
    Polyakova, Svetlana K.
    Balashova, Tatyana, V
    Rumyantcev, Roman, V
    Arsenyev, Maxim, V
    Fukin, Georgy K.
    Chesnokov, Sergey A.
    MENDELEEV COMMUNICATIONS, 2021, 31 (02) : 262 - 264
  • [29] Highly efficient photochemical generation of o-quinone methide from Mannich bases of phenol derivatives
    Nakatani, K
    Higashida, N
    Saito, I
    TETRAHEDRON LETTERS, 1997, 38 (28) : 5005 - 5008
  • [30] Stabilization and first direct spectroscopic evidence of the o-quinone methide derived from vitamin E
    Rosenau, T
    Potthast, A
    Elder, T
    Kosma, P
    ORGANIC LETTERS, 2002, 4 (24) : 4285 - 4288