Photochemical radical cyclization of γ,δ-unsaturated ketone oximes to 3,4-dihydro-2H-pyrroles

被引:44
作者
Kitamura, M [1 ]
Mori, Y [1 ]
Narasaka, K [1 ]
机构
[1] Univ Tokyo, Dept Chem, Grad Sch Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
oxime; radical cyclization; photoinduced electron transfer; photoinduced energy transfer;
D O I
10.1016/j.tetlet.2005.02.062
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3.4-Dihvdro-2H-pyrroles are synthesized from gamma,delta-unsaturated oximes by photochemical radical cyclization with 1,5-dimethoxynaphthatene (DMN) as the sensitizer. The cyclization of alkyl ketone O-acetyloximes proceeds via photosensitized electron transfer in the presence of acetic acid, while conjugated oximes of aryl and alpha,beta-unsaturated ketones are cyclized via energy transfer. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2373 / 2376
页数:4
相关论文
共 50 条
  • [1] IMINYLS .9. INTRAMOLECULAR ADDITION OF AN IMINYL TO AN ALKENE
    ATMARAM, S
    FORRESTER, AR
    GILL, M
    THOMSON, RH
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (06): : 1721 - 1724
  • [2] A NEW AND SYNTHETICALLY USEFUL SOURCE OF IMINYL RADICALS
    BOIVIN, J
    FOUQUET, E
    ZARD, SZ
    [J]. TETRAHEDRON LETTERS, 1991, 32 (34) : 4299 - 4302
  • [3] A new method for the generation and capture of iminyl radicals
    Boivin, J
    Schiano, AM
    Zard, SZ
    Zhang, HW
    [J]. TETRAHEDRON LETTERS, 1999, 40 (24) : 4531 - 4534
  • [4] IMINYL, AMIDYL, AND CARBAMYL RADICALS FROM O-BENZOYL OXIMES AND O-BENZOYL HYDROXAMIC ACID-DERIVATIVES
    BOIVIN, J
    CALLIERDUBLANCHET, AC
    QUICLETSIRE, B
    SCHIANO, AM
    ZARD, SZ
    [J]. TETRAHEDRON, 1995, 51 (23) : 6517 - 6528
  • [5] IMINYL RADICALS .3. FURTHER SYNTHETICALLY USEFUL SOURCES OF IMINYL RADICALS
    BOIVIN, J
    FOUQUET, E
    SCHIANO, AM
    ZARD, SZ
    [J]. TETRAHEDRON, 1994, 50 (06) : 1769 - 1776
  • [6] Bucher G, 2001, EUR J ORG CHEM, V2001, P545
  • [7] Chae KH, 1998, MACROMOL RAPID COMM, V19, P1
  • [8] Photosensitized reactions of oxime ethers: A steady-state and laser flash photolysis study
    de Lijser, HJP
    Tsai, CK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) : 3057 - 3067
  • [9] Free radical cyclizations involving nitrogen
    Fallis, AG
    Brinza, IM
    [J]. TETRAHEDRON, 1997, 53 (52) : 17543 - 17594
  • [10] HOMOLYTIC SUBSTITUTION BY IMINYL RADICAL AT SELENIUM - A FREE-RADICAL ROUTE TO 1,2-BENZOSELENAZOLES
    FONG, MC
    SCHIESSER, CH
    [J]. TETRAHEDRON LETTERS, 1993, 34 (27) : 4347 - 4348