The Oxidation of Amides to Imides: A Powerful Synthetic Transformation

被引：35
|
作者：
Sperry, Jonathan [1 ]
机构：
[1] Univ Auckland, Sch Chem Sci, Auckland 1, New Zealand
来源：
SYNTHESIS-STUTTGART | 2011年 / 22期
关键词：
imide; amide; oxidation; organic synthesis; RUTHENIUM TETROXIDE OXIDATION; ALPHA-AMINO-ACIDS; 1,3-DIPOLAR CYCLOADDITION REACTION; SUBSTITUTED CYCLIC IMIDES; FLUORESCENS DSM 11579; N-ACYL-PYRROLIDINES; STEREOSPECIFIC SYNTHESIS; BIOLOGICAL-ACTIVITY; AEROBIC PHOTOOXIDATION; ASYMMETRIC-SYNTHESIS;
D O I：
10.1055/s-0030-1260237
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Despite appearing to be a conceptually simple transformation, the oxidation of amides to imides is far from straightforward, primarily due to the inertness of amides toward electrophilic oxidants. This perspective provides an overview of the development of reaction conditions capable of effecting this oxidation. The application of amide to imide oxidations in the fields of medicinal chemistry and natural product synthesis, as well as the advantages and limitations of the various oxidation conditions, is also discussed.
引用
收藏
页码：3569 / 3580
页数：12
相关论文
共 50 条
  • [41] SYNTHESIS AND STRUCTURES OF (MONOORGANYL)AMIDES AND (MONOORGANYL)IMIDES OF ZIRCONIUM AND HAFNIUM
    BAI, YN
    ROESKY, HW
    NOLTEMEYER, M
    WITT, M
    CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (04): : 825 - 831
  • [42] NEW PHOTOOXIDATION - TRANSFORMATION OF LACTAMS INTO IMIDES
    GRAMAIN, JC
    REMUSON, R
    TROIN, Y
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (06) : 194 - 195
  • [43] PHOTOREACTIONS IN SYNTHESIS OF HETEROCYCLES - DESIGNS WITH AMIDES AND IMIDES AS SYNTHON CHROMOPHORES
    KANAOKA, Y
    HETEROCYCLES, 1977, 6 (9-10) : 1526 - 1530
  • [44] IR-SPECTRA OF AMIDES AND IMIDES OF DIVALENT AND TRIVALENT METALS
    LINDE, G
    JUZA, R
    ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1974, 409 (02): : 199 - 214
  • [45] ACYCLIC IMIDES . A GENERAL METHOD OF N-ACYLATION OF AMIDES
    BABURAO, K
    COSTELLO, AM
    PETTERSON, RC
    SANDER, GE
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (22): : 2779 - +
  • [46] Alkaline-earth amides and imides: Synthesis and structures.
    Vargas-Gregory, W
    Englich, U
    Ruhlandt-Senge, K
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U513 - U513
  • [47] SENSITIVE ION-EXCHANGE METHOD FOR DETECTION OF AMIDES AND IMIDES
    QURESHI, SZ
    IZZATULLAH, NN
    FRESENIUS ZEITSCHRIFT FUR ANALYTISCHE CHEMIE, 1977, 285 (3-4): : 265 - 265
  • [48] N-BROMINATION OF AMIDES, IMIDES, AND SULFONAMIDES WITH ACETYL HYPOBROMITE
    BEEBE, TR
    WOLFE, JW
    JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06): : 2056 - &
  • [49] AN ION-EXCHANGE METHOD FOR DETECTION OF AMIDES IMIDES AND ANILIDES
    WEST, PW
    QURESHI, M
    QURESHI, SZ
    ANALYTICA CHIMICA ACTA, 1966, 36 (01) : 97 - &
  • [50] Cyanomethylenetrimethylphosphorane, a powerful reagent for the Wittig olefination of esters, lactones and imides
    Tsunoda, T
    Takagi, H
    Takaba, D
    Kaku, H
    Itô, S
    TETRAHEDRON LETTERS, 2000, 41 (02) : 235 - 237
12345