Beckmann rearrangement: Thiamine hydrochloride as a remarkable catalyst for one-pot synthesis of amides from ketones

被引：16
|
作者：
Mahajan, Sheena [1 ]
Slathia, Nancy [1 ]
Kapoor, Kamal K. [1 ]
机构：
[1] Univ Jammu, Dept Chem, Jammu 180006, India
来源：
TETRAHEDRON LETTERS | 2020年 / 61卷 / 20期
关键词：
Beckmann rearrangement; Thiamine hydrochloride; Ketones; Amides; Acetamidocoumarin; ONE-STEP SYNTHESIS; CYCLOHEXANONE-OXIME; SOLVENT-FREE; ORGANIC-SYNTHESIS; NONCATALYTIC BECKMANN; SUPERCRITICAL WATER; EPSILON-CAPROLACTAM; EFFICIENT PROMOTER; REUSABLE CATALYST; IONIC LIQUIDS;
D O I：
10.1016/j.tetlet.2020.151859
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Thiamine hydrochloride catalyzed synthesis of amides from ketones including 3-acetyl coumarin via Beckmann rearrangement has been reported. The reaction is believed to involve oxime formation, cleavage of C-C bond followed by C-N bond formation in one-pot. Thiamine hydrochloride is stable, cheap, easy to handle and environmentally friendly. (C) 2020 Elsevier Ltd. All rights reserved.
引用
收藏
页数：5
相关论文
共 50 条
  • [21] Convenient One-Pot Synthesis of Allylsilanes from Enolizable Ketones
    Kwan, Man Lung D.
    Challen, Paul R.
    Tran, Quynh D-D
    SYNOPEN, 2019, 3 (04): : 138 - 141
  • [22] Scalable, one-pot synthesis of pyridazinones from azabicyclic ketones
    Sakurada, Isao
    Nguyen, Thuy P.
    Zhang, Lei
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
  • [23] An Efficient One-Pot Synthesis of ω-Hydroxy Ketones from Lactones
    Yang, Shao-Bo
    Gan, Feng-Feng
    Chen, Guo-Ju
    Xu, Peng-Fei
    SYNLETT, 2008, (16) : 2532 - 2534
  • [24] One-Pot Synthesis of (E)-Styryl Ketones from Styrenes
    Pawluc, Piotr
    Szudkowska, Justyna
    Hreczycho, Grzegorz
    Marciniec, Bogdan
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (15): : 6438 - 6441
  • [25] Chemoselective one-pot synthesis of β-keto sulfones from ketones
    Rawat, Vikas S.
    Reddy, Perla L. M.
    Sreedhar, Bojja
    RSC ADVANCES, 2014, 4 (10) : 5165 - 5168
  • [26] One-pot synthesis of N-imidoylbenzotriazoles via benzotriazole-mediated Beckmann rearrangement of oximes
    Katritzky, AR
    Monteux, DA
    Tymoshenko, DO
    ORGANIC LETTERS, 1999, 1 (04) : 577 - 578
  • [27] A one-pot synthesis of alkyl ferrocenyl ketones
    Vukicevic, RD
    Vukicevic, M
    Ratkovic, Z
    Konstantinovic, S
    SYNLETT, 1998, (12) : 1329 - 1330
  • [28] An efficient and versatile one-pot Beckmann rearrangement of ketoximes using mesitylenesulfonyl chloride
    Ramalingan, Chennan
    Park, Yong-Tae
    SYNTHESIS-STUTTGART, 2008, (09): : 1351 - 1358
  • [29] A one-pot synthesis of primary amides from aldoximes or aldehydes in water in the presence of a supported rhodium catalyst
    Fujiwara, Hiroshi
    Ogasawara, Yoshiyuki
    Yamaguchi, Kazuya
    Mizuno, Noritaka
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (27) : 5202 - 5205
  • [30] Copper(II) acetate-catalyzed one-pot conversion of aldehydes into primary amides through a Beckmann-type rearrangement
    Martinez-Asencio, Ana
    Yus, Miguel
    Ramon, Diego J.
    TETRAHEDRON, 2012, 68 (21) : 3948 - 3951
12345