Efficient synthesis of primary amides using 2-mercaptopyridone-1-oxide-based uronium salts

被引：33
作者：
Bailén, MA [1 ]
Chinchilla, R [1 ]
Dodsworth, DJ [1 ]
Nájera, C [1 ]
机构：
[1] Univ Alicante, Dept Quim Organ, E-03080 Alicante, Spain
来源：
TETRAHEDRON LETTERS | 2000年 / 41卷 / 50期
关键词：
aminium salts; primary amides; coupling reagents;
D O I：
10.1016/S0040-4039(00)01775-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
S-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium tetrafluoroborate (TOTT) and hexafluorophosphate (HOTT) are cheap and convenient reagents for the rapid and high-yielding preparation of primary amides when reacted with carboxylic acids and ammonium chloride in the presence of diisopropylethylamine. The reaction is chemoselective and undesired ammonolysis of other sensitive functional groups is not observed. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：9809 / 9813
页数：5
相关论文
共 22 条
  • [1] Stereoselective Pseudomonas cepacia lipase mediated synthesis of alpha-hydroxyamides
    Adamczyk, M
    Grote, J
    Rege, S
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (15) : 2509 - 2512
  • [2] 2-mercaptopyridone 1-oxide-based uronium salts:: New peptide coupling reagents
    Bailén, MA
    Chinchilla, R
    Dodsworth, DJ
    Nájera, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (24) : 8936 - 8939
  • [3] BIANCHI M, 1965, FARMACO-ED SCI, V20, P611
  • [4] Brown W, 1999, IDrugs, V2, P1059
  • [5] CHARACTERIZATION OF A SYNTHETIC PEPTIDE IMPURITY BY FAST-ATOM-BOMBARDMENT TANDEM MASS-SPECTROMETRY AND GAS-CHROMATOGRAPHY MASS-SPECTROMETRY
    BURINSKY, DJ
    DUNPHY, R
    OYLER, AR
    SHAW, CJ
    COTTER, ML
    [J]. JOURNAL OF PHARMACEUTICAL SCIENCES, 1992, 81 (06) : 597 - 600
  • [6] CASADEI MA, 1991, B SOC CHIM FR, P54
  • [7] (E)-5-tosyl-4-pentenamide: A vinyl sulfone for the one-pot general synthesis of indolizidine derivatives
    Caturla, F
    Najera, C
    [J]. TETRAHEDRON LETTERS, 1997, 38 (21) : 3789 - 3792
  • [8] CHEN ST, 1989, SYNTHESIS-STUTTGART, P37
  • [9] S-(1-oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium hexafluorophosphate.: A new reagent for preparing hindered Barton esters
    Garner, P
    Anderson, JT
    Dey, S
    Youngs, WJ
    Galat, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) : 5732 - 5733
  • [10] BIOSYNTHESIS OF BERNINAMYCIN - INCORPORATION OF C-13-LABELED AMINO-ACIDS
    LAU, RCM
    RINEHART, KL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (29) : 7606 - 7610
123