Synthesis of 2-unsubstituted imidazolones from bisamides via a one-pot, domino dehydration/base promoted cyclisation process

被引：3
作者：
Djukanovic, Dimitrije [1 ]
Petkovic, Milos [1 ]
Simic, Milena [1 ]
Jovanovic, Predrag [1 ]
Tasic, Gordana [1 ]
Savic, Vladimir [1 ]
机构：
[1] Univ Belgrade, Fac Pharm, Dept Organ Chem, Vojvode Stepe 450, Belgrade 11221, Serbia
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 10期
关键词：
Imidazolones; Bisamides; One-pot cyclisation; IMIDAZOLINONE HERBICIDES; BIOLOGICAL EVALUATION; DERIVATIVES; EFFICIENT; GFP; ANTIHYPERTENSION; ISOCYANIDES; ANTAGONISTS; ANALOGS; AMINO;
D O I：
10.1016/j.tetlet.2018.01.074
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A one-pot, domino process was developed as an alternative approach for the preparation of 2-unsubstituted imidazolones. The methodology utilizes readily accessible bisamides, which upon a dehydration/-cyclisation sequence produced imidazolones in good yields. The transformation relies on the compatibility of the dehydrating agent and base, and the reaction conditions tolerate various functional groups. (C) 2018 Elsevier Ltd. All rights reserved.
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收藏
页码：914 / 917
页数：4
相关论文
共 32 条
  • [1] Synthesis of dimethyl derivatives of imidazolinone herbicides: Their use in efficient gas chromatographic methods for the determination of these herbicides
    Anisuzzaman, AKM
    Amin, M
    Ogg, N
    Hoq, F
    Kanithi, MR
    Jenkins, RE
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (12) : 5893 - 5902
  • [2] Synthesis and evaluation of novel angiotensin II receptor 1 antagonists as anti-hypertension drugs
    Bao, Xiaolu
    Zhu, Weibo
    Zhang, Ruijing
    Wen, Caihong
    Wang, Li
    Yan, Yijia
    Tang, Hesheng
    Chen, Zhilong
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (09) : 2023 - 2031
  • [3] Diversified Aminohydantoins from Ureas and Thioureas Tethered to Amides
    Bepary, Sukumar
    Youn, In Kwon
    Lim, Hee-Jong
    Lee, Ge Hyeong
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (13) : 2542 - 2548
  • [4] Application of isocyanides derived from α-amino acids as substrates for the Ugi reaction
    Berlozecki, Stanislaw
    Szymanski, Wiktor
    Ostaszewski, Ryszard
    [J]. SYNTHETIC COMMUNICATIONS, 2008, 38 (16) : 2714 - 2721
  • [5] A NEW SERIES OF IMIDAZOLONES - HIGHLY SPECIFIC AND POTENT NONPEPTIDE AT(1) ANGIOTENSIN-II RECEPTOR ANTAGONISTS
    BERNHART, CA
    PERREAUT, PM
    FERRARI, BP
    MUNEAUX, YA
    ASSENS, JLA
    CLEMENT, J
    HAUDRICOURT, F
    MUNEAUX, CF
    TAILLADES, JE
    VIGNAL, MA
    GOUGAT, J
    GUIRAUDOU, PR
    LACOUR, CA
    ROCCON, A
    CAZAUBON, CF
    BRELIERE, JC
    LEFUR, G
    NISATO, D
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (22) : 3371 - 3380
  • [6] Bignan G C, 2014, [No title captured], Patent No. [WO 2014/039769, 2014039769, WO 2014039769]
  • [7] Tuning the Electronic Properties of Carbenes: A Systematic Comparison of Neighboring Amino versus Amido Groups
    Blake, Garrett A.
    Moerdyk, Jonathan P.
    Bielawski, Christopher W.
    [J]. ORGANOMETALLICS, 2012, 31 (08) : 3373 - 3378
  • [8] STUDIES ON ISOCYANIDES AND RELATED-COMPOUNDS - A CONVENIENT SYNTHESIS OF 2,3-DISUBSTITUTED SPIROIMIDAZOLONES
    BOSSIO, R
    MARCACCINI, S
    PAPALEO, S
    PEPINO, R
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (02) : 397 - 399
  • [9] Bossio R, 1991, SYNTHESIS-STUTTGART, P843
  • [10] β-Cyclodextrin as a mimetic of the natural GFP-chromophore environment
    Cacciarini, Martina
    Nielsen, Mogens Brondsted
    de Castro, Elisa Martinez
    Marinescu, Lavinia
    Bols, Mikael
    [J]. TETRAHEDRON LETTERS, 2012, 53 (08) : 973 - 976
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