Termination of Mn(III)-based oxidative cyclizations by trapping with azide

被引:38
|
作者
Snider, BB [1 ]
Duvall, JR [1 ]
机构
[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA
关键词
D O I
10.1021/ol049805s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The radicals formed in Mn(III)-based oxidative free-radical cyclizations of beta-keto esters and malonate esters can be trapped with sodium azide and Mn(ill) to give cyclic and bicyclic azides in 30-80% yield. Reduction of the azide gives bi- and tricyclic lactams.
引用
收藏
页码:1265 / 1268
页数:4
相关论文
共 50 条
  • [31] MN(III)-BASED OXIDATIVE FREE-RADICAL CYCLIZATION OF UNSATURATED-KETONES
    SNIDER, BB
    COLE, BM
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17): : 5376 - 5377
  • [32] Oxidative DNA cleavage catalyzed by Mn(III) corroles
    Liu Hai-Yang
    Liu Lan-Ying
    Zhang Lei
    Ying Xiao
    Wang Xiang-Li
    Jiang Huan-Feng
    Chang Chi-Kwong
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2007, 28 (09): : 1628 - 1630
  • [33] Trapping of the dichlorocarbonyl oxide using a chiral (salen)Mn (III) complex
    Lee, NH
    Baik, JS
    Han, SB
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1997, 18 (08) : 796 - 798
  • [34] ASPECTS OF MANGANESE(III) - PROMOTED OXIDATIVE FREE-RADICAL CYCLIZATIONS TO FUNCTIONALIZED BICYCLIC SYSTEMS
    ZORETIC, PA
    RAMCHANDANI, M
    CASPAR, ML
    SYNTHETIC COMMUNICATIONS, 1991, 21 (07) : 915 - 922
  • [35] Synthesis of dioxapropellanes using Mn(III)-based oxidative tandem cyclization of tetracarbonyl compounds with diarylethenes
    Shibuya, Keisuke
    Chikamatsu, Ayaka
    Hisano, Kazuki
    Nishino, Hiroshi
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2024, 97 (03)
  • [36] FACILE SYNTHESIS OF INDOLELACTONES USING Mn(III)-BASED OXIDATIVE SUBSTITUTION-CYCLIZATION REACTION
    Inoue, Takeshi
    Nishino, Hiroshi
    HETEROCYCLES, 2018, 97 (01) : 431 - 450
  • [37] CYCLIZATIONS OF UNSATURATED.CR(COX)2 RADICALS - MANGANESE(III) ACETATE OXIDATIVE CYCLIZATIONS OF UNSATURATED ACETOACETATES AND ATOM-TRANSFER CYCLIZATIONS OF UNSATURATED HALOACETOACETATES GIVE THE SAME RADICALS
    CURRAN, DP
    MORGAN, TM
    SCHWARTZ, CE
    SNIDER, BB
    DOMBROSKI, MA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (17) : 6607 - 6617
  • [38] PHOTOCATALYTIC SYSTEMS .25. SPIN TRAPPING OF AZIDE RADICALS IN PHOTOLYSIS OF AZIDO COBALT(III) COMPLEXES
    REHOREK, D
    THOMAS, P
    HENNIG, H
    INORGANICA CHIMICA ACTA, 1979, 32 (01) : L1 - L2
  • [39] Mn(III) Hexafluoroacetylacetonate as an Oxidative Agent in the Synthesis of Heterobimetallic β-Diketonates
    Haitao Zhang
    Bo Li
    Evgeny V. Dikarev
    Journal of Cluster Science, 2008, 19 : 311 - 321
  • [40] Oxidative Formation and Removal of Complexed Mn(III) by Pseudomonas Species
    Wright, Mitchell H.
    Geszvain, Kati
    Oldham, Veronique E.
    Luther, George W., III
    Tebo, Bradley M.
    FRONTIERS IN MICROBIOLOGY, 2018, 9