Selenium-Nitrogen Bond Cleavage in Selenazole Ring System with Grignard Reagent: A Convenient Synthesis of Unsymmetrically Substituted Selenides

被引:7
作者
Lisiak, Rafal [1 ]
Mlochowski, Jacek [1 ]
机构
[1] Wroclaw Univ Technol, Fac Chem, Dept Organ Chem, PL-50370 Wroclaw, Poland
关键词
Grignard reagents; heterocycles; selenenamides; selenides; DIORGANYL SELENIDES; ALLYLIC ALCOHOLS; SE-SE; SELENOXIDE; CONVERSION; OXIDATION; HALIDES; ANIONS; ACIDS;
D O I
10.1080/00397910902730994
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
High reactivity of the selenenamide bond in selenazoles toward nucleophiles can be exploited for synthesis of other organoselenium compounds. It has been found that benzisoselenazol-3(2H)-ones and related selenaheterocycles with an Se-N moiety treated with Grignard reagent gave unsymmetrical aryl-aryl and aryl-alkyl selenides in moderate to good yields. This reaction has a synthetic value because it is highly selective and can be realized under mild conditions.
引用
收藏
页码:3141 / 3155
页数:15
相关论文
共 29 条
  • [1] Efficient synthesis of diorganyl selenides via cleavage of Se-Se bond of diselenides by indium(III) catalyst and zinc
    Braga, Antonio L.
    Schneider, Paulo H.
    Paixao, Marcio W.
    Deobald, Anna M.
    [J]. TETRAHEDRON LETTERS, 2006, 47 (40) : 7195 - 7198
  • [2] A STUDY ON THE REDUCING ABILITIES OF TRIS(ALKYLTHIO)SILANES
    CHATGILIALOGLU, C
    GUERRA, M
    GUERRINI, A
    SECONI, G
    CLARK, KB
    GRILLER, D
    KANABUSKAMINSKA, J
    MARTINHOSIMOES, JA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) : 2427 - 2433
  • [3] DALLACKER F, 1991, CHEM ZTG, V115, P169
  • [4] One-pot oxidation of azomethine compounds into arenecarboxylic acids
    Giurg, M
    Said, SB
    Syper, L
    Mlochowski, J
    [J]. SYNTHETIC COMMUNICATIONS, 2001, 31 (20) : 3151 - 3159
  • [5] SYNTHETIC APPLICATIONS OF ARYLSELENENIC AND ARYLSELENINIC ACIDS - CONVERSION OF OLEFINS TO ALLYLIC ALCOHOLS AND EPOXIDES
    HORI, T
    SHARPLESS, KB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (09) : 1689 - 1697
  • [6] Facile Photochemical Transformation of Alkyl Aryl Selenides to the Corresponding Carbonyl Compounds by Molecular Oxygen: Use of Selenides as Masked Carbonyl Groups
    Hyugano, Takeshi
    Liu, Suyou
    Ouchi, Akihiko
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) : 8861 - 8866
  • [7] Kloc K, 1999, EUR J ORG CHEM, V1999, P67, DOI 10.1002/(SICI)1099-0690(199901)1999:1<67::AID-EJOC67>3.0.CO
  • [8] 2-Q
  • [9] New heterocyclic selenenamides:: 1,2,4-benzoselenadiazin-3(4H)-ones and 1,3,2-benzodiselenazoles
    Kloc, K
    Mlochowski, J
    Osajda, K
    Syper, L
    Wójtowicz, H
    [J]. TETRAHEDRON LETTERS, 2002, 43 (22) : 4071 - 4074
  • [10] KORCHEVIN NA, 1990, J GEN CHEM USSR, V60, P1495