Synthesis of Diverse Ureas from Amines and CO2 at Atmospheric Pressure and Room Temperature

被引:0
作者
Gou, Wenchang [1 ]
Dai, Pinli [1 ]
Wang, Mei [1 ]
Wang, Yunhuan [1 ]
Ma, Nana [1 ]
Zhou, Xuan [1 ]
Xu, Yingjian [2 ]
Zhang, Lin [1 ]
Li, Chun [1 ]
机构
[1] Guizhou Med Univ, Sch Pharmaceut Sci, Guiyang 550004, Peoples R China
[2] GoldenKeys High tech Mat Co Ltd, Guiyang 550025, Guizhou, Peoples R China
基金
中国国家自然科学基金;
关键词
CARBON-DIOXIDE; EFFICIENT SYNTHESIS; UNSYMMETRICAL UREAS; DERIVATIVES; DISCOVERY; CATALYST; BENZIMIDAZOLONES; CARBONYLATION; CYCLIZATION; PENCYCURON;
D O I
10.1021/acs.joc.4c01474
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free method is developed to perform the synthesis of urea derivatives utilizing CO2 as the C1 building block at atmospheric pressure and room temperature. In addition to diverse symmetric and dissymmetric ureas, benzimidazolones and quinazolinone can also be easily prepared using this protocol. Most importantly, the gram-scale preparation of fungicide pencycuron and antipsychotic drug pimavanserin proceeded smoothly under the mild conditions.
引用
收藏
页码:12498 / 12507
页数:10
相关论文
共 73 条
  • [1] Nitrogen fertilization and foliar urea effects on durum wheat yield and quality and on residual soil nitrate in irrigated Mediterranean conditions
    Abad, A
    Lloveras, J
    Michelena, A
    [J]. FIELD CROPS RESEARCH, 2004, 87 (2-3) : 257 - 269
  • [2] A One-Pot Synthesis of Symmetrical and Unsymmetrical Dipeptide Ureas
    Abou Fayad, Antoine
    Pubill-Ulldemolins, Cristina
    Sharma, Sunil V.
    Day, David
    Goss, Rebecca J. M.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (25) : 5603 - 5609
  • [3] QUINOXALINE DERIVATIVES .X. A NOVEL REARRANGEMENT OF CERTAIN QUINOXALINE N-OXIDES TO 2-BENZIMIDAZOLINONES
    AHMAD, Y
    HABIB, MS
    MOHAMMAD.A
    BAKHTIAR.B
    SHAMSI, SA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (01) : 201 - &
  • [4] Design, Synthesis, Molecular Docking, and Biological Evaluation of Novel Pimavanserin-Based Analogues as Potential Serotonin 5-HT2A Receptor Inverse Agonists
    Albujuq, Nader R.
    Meana, J. Javier
    Diez-Alarcia, Rebeca
    Muneta-Arrate, Itziar
    Naqvi, Arshi
    Althumayri, Khalid
    Alsehli, Mosa
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2023, 66 (13) : 9057 - 9075
  • [5] Untargeted Screening in a Case Control Study Using Apples as a Matrix
    Bakota, Erica L.
    Levine, Robert A.
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2020, 68 (37) : 10232 - 10246
  • [6] Potassium Hydroxide/Dimethyl Sulfoxide Promoted Intramolecular Cyclization for the Synthesis of Benzimidazol-2-ones
    Beyer, Astrid
    Reucher, Christine M. M.
    Bolm, Carsten
    [J]. ORGANIC LETTERS, 2011, 13 (11) : 2876 - 2879
  • [7] Reaction of aliphatic amines with acetoacetanilide in the presence of zeolite catalyst.: Solvent-free synthesis of symmetric N,N′-dialkylureas
    Bigi, F
    Frullanti, B
    Maggi, R
    Sartori, G
    Zambonin, E
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) : 1004 - 1006
  • [8] Pharmacological characterization of a new series of carbamoylguanidines reveals potent agonism at the H2R and D3R
    Biselli, Sabrina
    Bresinsky, Merlin
    Tropmann, Katharina
    Forster, Lisa
    Honisch, Claudia
    Buschauer, Armin
    Bernhardt, Gunther
    Pockes, Steffen
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2021, 214
  • [9] Urea- and Thiourea-Catalyzed Aminolysis of Carbonates
    Blain, Marine
    Yau, Honman
    Jean-Gerard, Ludivine
    Auvergne, Remi
    Benazet, Dominique
    Schreiner, Peter R.
    Caillol, Sylvain
    Andrioletti, Bruno
    [J]. CHEMSUSCHEM, 2016, 9 (16) : 2269 - 2272
  • [10] A novel synthesis of isocyanates and ureas via β-elimination of haloform
    Braverman, S
    Cherkinsky, M
    Kedrova, L
    Reiselman, A
    [J]. TETRAHEDRON LETTERS, 1999, 40 (16) : 3235 - 3238