Cyanuric chloride: an efficient reagent for the Lossen rearrangement

被引:47
作者
Hamon, Florian [1 ]
Prie, Gildas [1 ]
Lecornue, Frederic [1 ]
Papot, Sebastien [1 ]
机构
[1] Univ Poitiers, UMR CNRS 6514, F-86022 Poitiers, France
关键词
Lossen rearrangement; Cyanuric chloride; Hydroxamic acids; Isocyanates; BECKMANN REARRANGEMENT; HYDROXAMIC ACIDS; MILD; OXIMES;
D O I
10.1016/j.tetlet.2009.09.115
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for the Lossen rearrangement that uses 2,4,6-trichloro-1,3,5-triazine (TCT) as a promoter is reported. This procedure allowed the preparation of various carbamates, thiocarbamates, and ureas in good yields directly from the corresponding hydroxamic acids. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6800 / 6802
页数:3
相关论文
共 18 条
  • [1] N,O-Bis-(ethoxycarbonyl)hydroxylamine:: a convenient reagent for the Lossen transformation
    Anilkumar, R
    Chandrasekhar, S
    Sridhar, M
    [J]. TETRAHEDRON LETTERS, 2000, 41 (27) : 5291 - 5293
  • [2] Synthesis of acyl azides from carboxylic acids using cyanuric chloride
    Bandgar, BP
    Pandit, SS
    [J]. TETRAHEDRON LETTERS, 2002, 43 (18) : 3413 - 3414
  • [3] STEREOSPECIFIC LOSSEN REARRANGEMENTS
    BAUER, L
    MIARKA, SV
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (09) : 1293 - 1296
  • [4] CHEMISTRY OF HYDROXAMIC ACIDS AND N-HYDROXYIMIDES
    BAUER, L
    EXNER, O
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1974, 13 (06) : 376 - 384
  • [5] Beckmann rearrangement of oximes catalyzed by cyanuric chloride in ionic liquids
    Betti, Cecilia
    Landini, Dario
    Maia, Angelamaria
    Pasia, Maurizio
    [J]. SYNLETT, 2008, (06) : 908 - 910
  • [6] Recent applications of 2,4,6-trichloro-1,3,5-triazine and its derivatives in organic synthesis
    Blotny, Grzegorz
    [J]. TETRAHEDRON, 2006, 62 (41) : 9507 - 9522
  • [7] A mild and general method for preparation of α-glycosyl chlorides
    Chang, Chih-Wei
    Chang, Shih-Sheng
    Chao, Chin-Sheng
    Mong, Kwok-Kong T.
    [J]. TETRAHEDRON LETTERS, 2009, 50 (31) : 4536 - 4540
  • [8] Beckmann rearrangement of oximes under very mild conditions
    De Luca, L
    Giacomelli, G
    Porcheddu, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17) : 6272 - 6274
  • [9] A mild and efficient alternative to the classical swern oxidation
    De Luca, L
    Giacomelli, G
    Porcheddu, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) : 7907 - 7909
  • [10] A new and efficient route toward the preparation of diazo ketones using cyanuric chloride and diazomethane
    Forbes, DC
    Barrett, EJ
    Lewis, DL
    Smith, MC
    [J]. TETRAHEDRON LETTERS, 2000, 41 (51) : 9943 - 9947