Visible-Light-Mediated Oxidation of 1-Benzyl-3,4-dihydroisoquinolines with Dioxygen: A Switchable Synthesis of 1-Benzoylisoquinolines and 1-Benzoyl-3,4-dihydroisoquinolines

被引：2
|
作者：
Ma, Peipei [1 ]
Wu, Hongli [1 ]
Gan, Haifeng [1 ]
机构：
[1] Nanjing Tech Univ, Coll Biotechnol & Pharmaceut Engn, 30 South Puzhu Rd, Nanjing 211816, Jiangsu, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2023年 / 55卷 / 24期
基金：
中国国家自然科学基金;
关键词：
visible light; 1-benzoylisoquinolines; 1-benzoyl-3,4-dihydroisoquinolines; metal-free; dioxygen; N-HETEROCYCLES; ISOQUINOLINE ALKALOIDS; FREE ACYLATION; C-C; TANDEM; BENZYLISOQUINOLINE; PHOTOCATALYST; OXOAPORPHINE; QUINOLINES; AMIDATION;
D O I：
10.1055/a-2160-8903
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A visible-light-mediated metal-free oxidation of 1-benzyl-3,4-dihydroisoquinolines (1-BnDHIQs) for the switchable preparation of a wide range of 1-benzoylisoquinolines (BzIQs) and 1-benzoyl-3,4-dihydroisoquinolines (BzDHIQs) is realized using dioxygen as the oxidant. This protocol provides a facile route for the efficient synthesis of isoquinoline alkaloids. Mechanistic investigations suggest that a radical pathway and an ionic pathway may exist simultaneously, with both pathways proceeding via a common key peroxide intermediate to give the oxidized products.
引用
收藏
页码：4103 / 4112
页数：10
相关论文
共 50 条
  • [1] A COLOUR REACTION OF 1-BENZOYL-3,4-DIHYDROISOQUINOLINES
    BUDZIKIEWICZ, H
    KRUGER, U
    SASSE, WD
    WIEGREBE, W
    ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1970, 737 : 119 - +
  • [2] FORMYLATION OF METHYLENE GROUPS IN 1-BENZYL-3,4-DIHYDROISOQUINOLINES
    THUAN, NTL
    GARDENT, J
    COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1968, 267 (26): : 1848 - &
  • [3] OXIDATION OF 1-BENZYL-3,4-DIHYDROISOQUINOLINES USING ACTIVE MANGANESE-DIOXIDE
    AMARAVATHI, M
    KUMARI, LK
    PARDHASARADHI, M
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1983, 22 (12): : 1246 - 1247
  • [4] REGIOSPECIFIC OXIDATION OF SUBSTITUTED 1-BENZYL-3,4-DIHYDROISOQUINOLINES USING SINGLET OXYGEN
    MARTIN, NH
    CHAMPION, SL
    BELT, PB
    TETRAHEDRON LETTERS, 1980, 21 (27) : 2613 - 2616
  • [5] LEAD-TETRAACETATE MEDIATED OXIDATION OF THE ENAMIDES DERIVED FROM 1-BENZYL-3,4-DIHYDROISOQUINOLINES
    LENZ, GR
    COSTANZA, C
    JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06): : 1176 - 1183
  • [6] TRANSFORMATION OF 1-BENZYL-3,4-DIHYDROISOQUINOLINES IN 13-FORMYL-PROTOBERBERINIUM SALTS
    THUAN, NTL
    GARDENT, J
    COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1969, 268 (01): : 86 - &
  • [7] Synthesis of 1-aroyl-3,4-dihydroisoquinolines
    Mikhailovsky, AG
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2000, (02): : 264 - 265
  • [8] Oxidation of substituted 1-benzyl-3 4-dihydroisoquinolines and synthesis of papaveraldine
    Buck, JS
    Haworth, RD
    Perkin, WH
    JOURNAL OF THE CHEMICAL SOCIETY, 1924, 125 : 2176 - 2185
  • [9] Azocoupling reaction of 1-benzyl-3,4-dihydroisoquinolines with diazonium salts and the properties of its products
    O. V. Surikova
    A. G. Mikhailovskii
    E. V. Vikhareva
    M. I. Vakhrin
    Chemistry of Heterocyclic Compounds, 2008, 44 : 184 - 189
  • [10] Azocoupling reaction of 1-benzyl-3,4-dihydroisoquinolines with diazonium salts and the properties of its products
    Surikova, O. V.
    Mikhailovskii, A. G.
    Vikhareva, E. V.
    Vakhrin, M. I.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (02) : 184 - 189
12345