Photochemistry of acyloximes: synthesis of heterocycles and natural products

被引:50
作者
Alonso, Rafael [1 ]
Caballero, Alegria [1 ]
Campos, Pedro J. [1 ]
Rodriguez, Miguel A. [1 ]
机构
[1] Univ La Rioja, Dept Quim, Grp Sintesis Quim La Rioja, Unidad Asociada,CSIC, Logrono 26006, Spain
关键词
Acyloxime; Radical; Cyclization; Heterocycles; FREE-RADICAL CYCLIZATIONS; IMINYL RADICALS; OXIMES; DIHYDROPYRROLES;
D O I
10.1016/j.tet.2010.09.078
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New applications of the photochemically generated iminyl radicals ring closure onto phenyl, thiophenyl, and pyridinyl rings are presented. The influence on the reactivity of different substituent throughout the acyloxime structure is discussed. Some observed effects are interpreted from computational studies. This reaction provides a new, simple, and straightforward method for the preparation of several polycyclic heteroaromatic compounds and it has been applied to the synthesis of some natural products. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8828 / 8831
页数:4
相关论文
共 19 条
  • [1] Photocyclization of iminyl radicals:: Theoretical study and photochemical aspects
    Alonso, Rafael
    Campos, Pedro J.
    Rodriguez, Miguel A.
    Sampedro, Diego
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (06) : 2234 - 2239
  • [2] New light-induced iminyl radical cyclization reactions of acyloximes to isoquinolines
    Alonso, Rafael
    Campos, Pedro J.
    Garcia, Barbara
    Rodriguez, Miguel A.
    [J]. ORGANIC LETTERS, 2006, 8 (16) : 3521 - 3523
  • [3] Tin-free radical cyclizations for the synthesis of 7-azaoxindoles, 7-azaindolines, tetrahydro[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b]azepin-8-ones
    Bacqué, E
    El Qacemi, M
    Zard, SZ
    [J]. ORGANIC LETTERS, 2004, 6 (21) : 3671 - 3674
  • [4] Free radical cyclizations involving nitrogen
    Fallis, AG
    Brinza, IM
    [J]. TETRAHEDRON, 1997, 53 (52) : 17543 - 17594
  • [5] Frisch M. J., 2004, GAUSSIAN 03 REVISION
  • [6] Gagosz F, 1999, SYNLETT, P1978
  • [7] Photochemical radical cyclization of γ,δ-unsaturated ketone oximes to 3,4-dihydro-2H-pyrroles
    Kitamura, M
    Mori, Y
    Narasaka, K
    [J]. TETRAHEDRON LETTERS, 2005, 46 (14) : 2373 - 2376
  • [8] Radical Synthesis of Guanidines from N-Acyl Cyanamides
    Larraufie, Marie-Helene
    Ollivier, Cyril
    Fensterbank, Louis
    Malacria, Max
    Lacote, Emmanuel
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (12) : 2178 - 2181
  • [9] Photochemical transformation of γ,δ-unsaturated ketone O-(p-cyanophenyl) oximes to 3,4-dihydro-2H-pyrrole derivatives
    Mikami, T
    Narasaka, K
    [J]. CHEMISTRY LETTERS, 2000, (04) : 338 - 339
  • [10] From dioxime oxalates to dihydropyrroles and phenanthridines via iminyl radicals
    Portela-Cubillo, Fernando
    Scanlan, Eoin M.
    Scott, Jackie S.
    Walton, John C.
    [J]. CHEMICAL COMMUNICATIONS, 2008, (35) : 4189 - 4191