ORTHO-(ALPHA-BENZOTRIAZOLYLALKYL)PHENOLS - NOVEL PRECURSORS OF ORTHO-QUINONE METHIDES

被引:0
|
作者
KATRITZKY, AR [1 ]
LAN, XF [1 ]
机构
[1] UNIV FLORIDA,CTR HETEROCYCL CPDS,GAINESVILLE,FL 32611
来源
SYNTHESIS-STUTTGART | 1992年 / 08期
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1-[alpha-(Benzotriazol-1-yl)alkyl]-2-napthols and 2-[(benzotriazol-1-yl)-methyl]phenols have been shown to lose a molecule of benzotriazole to generate o-quinone methides, which can be trapped with electron-rich olefins (ethyl vinyl ether, 1-vinyl-2-pyrrolidinone) to afford chroman derivatives, i.e. 2,3-dihydro-1H-naphtho[2,1-b]pyrans and 3,4-dihydro-2H-1-benzopyrans, respectively.
引用
收藏
页码:761 / 764
页数:4
相关论文
共 50 条
  • [21] Diphosphination of ortho-quinone methide precursors with diphosphines
    Kato, Yugo
    Otomura, Nobutaka
    Hirano, Koji
    Miura, Masahiro
    TETRAHEDRON LETTERS, 2019, 60 (30) : 2014 - 2017
  • [22] Chemoselective oxidative generation of ortho-quinone methides and tandem transformations
    Muhammet Uyanik
    Kohei Nishioka
    Ryutaro Kondo
    Kazuaki Ishihara
    Nature Chemistry, 2020, 12 : 353 - 362
  • [23] Defining the Synthetic Scope of ortho-Quinone Methides by Quantifying their Electrophilicity
    Gross, Christoph
    Eitzinger, Andreas
    Hampel, Nathalie
    Mayer, Peter
    Ofial, Armin R.
    Chemistry - A European Journal, 2024,
  • [24] Harnessing ortho-Quinone Methides in Natural Product Biosynthesis and Biocatalysis
    Purdy, Trevor N.
    Moore, Bradley S.
    Lukowski, April L.
    JOURNAL OF NATURAL PRODUCTS, 2022, 85 (03): : 688 - 701
  • [25] Chemoselective oxidative generation of ortho-quinone methides and tandem transformations
    Uyanik, Muhammet
    Nishioka, Kohei
    Kondo, Ryutaro
    Ishihara, Kazuaki
    NATURE CHEMISTRY, 2020, 12 (04) : 353 - +
  • [26] Michael Additions of Highly Basic Enolates to ortho-Quinone Methides
    Lewis, Robert S.
    Garza, Christopher J.
    Dang, Ann T.
    Pedro, Te Kie A.
    Chain, William J.
    ORGANIC LETTERS, 2015, 17 (09) : 2278 - 2281
  • [27] Catalyst-free thiophosphorylation of in situ formed ortho-quinone methides
    Ash, Jeffrey
    Kang, Jun Yong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (11) : 2370 - 2374
  • [28] Mannich base-connected syntheses mediated by ortho-quinone methides
    Barta, Petra
    Fulop, Ferenc
    Szatmari, Istvan
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 : 560 - 575
  • [29] QUINONE METHIDES AND FUCHSONES .19. DELOCALIZATION AND STABILITY OF ORTHO-QUINONE AND PARA-QUINONE METHIDES - A HMO STUDY
    MUSIL, L
    KOUTEK, B
    PISOVA, M
    SOUCEK, M
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1981, 46 (05) : 1148 - 1159
  • [30] Phosphine-catalysed transformations of ortho- and para-quinone methides
    Maestro, Aitor
    Zurro, Mercedes
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (41) : 8244 - 8258