Facile one-pot synthesis of unsymmetrical ureas, carbamates, and thiocarbamates from Cbz-protected amines

被引:31
|
作者
Kim, Hee-Kwon [1 ,2 ]
Lee, Anna [3 ]
机构
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
[2] Chonbuk Natl Univ, Med Sch & Hosp, Biomed Res Inst, Mol Imaging & Therapeut Med Res Ctr,Dept Nucl Med, Jeonju 54907, Jeonbuk, South Korea
[3] Myongji Univ, Dept Chem, Yongin 17058, South Korea
关键词
PROTEASE INHIBITORS; ELEMENTAL SULFUR; DISCOVERY; AMIDES; ACETONITRILE; DERIVATIVES; DIPEPTIDES; CONVERSION; HYDROLYSIS; CONVENIENT;
D O I
10.1039/c6ob01290f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel one-pot synthesis of unsymmetrical ureas, carbamates and thiocarbamates from Cbz-protected amines has been developed. In the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, isocyanates are generated in situ, which facilitate rapid reaction with amines, alcohols, and thiols to afford the corresponding ureas, carbamates and thiocarbamates in high yields.
引用
收藏
页码:7345 / 7353
页数:9
相关论文
共 50 条
  • [1] One-pot synthesis of carbamates and thiocarbamates from Boc-protected amines
    Kim, Hee-Kwon
    Lee, Anna
    TETRAHEDRON LETTERS, 2016, 57 (44) : 4890 - 4892
  • [2] One-Pot Synthesis of Ureas from Boc-Protected Amines
    Spyropoulos, Constantinos
    Kokotos, Christoforos G.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10): : 4477 - 4483
  • [3] Direct synthesis of carbamates, thiocarbamates, and ureas from Boc-protected amines: a sustainable and efficient approach
    Li, Wanyong
    Lv, Mengting
    Luo, Xiaolin
    Wang, Zhouyu
    Song, Qiao
    Yu, Xiaoqi
    RSC ADVANCES, 2024, 14 (29) : 20656 - 20659
  • [4] 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.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (25) : 5603 - 5609
  • [5] Facile One-Pot Synthesis of Substituted Hydantoins from Carbamates
    Tanwar, Dinesh Kumar
    Ratan, Anjali
    Gill, Manjinder Singh
    SYNLETT, 2017, 28 (17) : 2285 - 2290
  • [6] An efficient one pot synthesis of N,N'-disubstituted unsymmetrical ureas and carbamates
    Choy, N
    Moon, KY
    Park, C
    Son, YC
    Jung, WH
    Choi, HI
    Lee, CS
    Kim, CR
    Kim, SC
    Yoon, H
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1996, 28 (02) : 173 - 177
  • [7] Facile one-pot synthesis of S-alkyl thiocarbamates
    Wynne, JH
    Jensen, SD
    Snow, AW
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (09): : 3733 - 3735
  • [8] One-Pot Synthesis of Thiocarbamates
    Waibel, Kevin A.
    Barther, Dennis
    Malliaridou, Triantafillia
    Moatsou, Dafni
    Meier, Michael A. R.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (31) : 4508 - 4516
  • [9] A simple one-pot preparation of N,N'-unsymmetrical ureas from N-Boc protected primary anilines and amines
    Lamothe, M
    Perez, M
    ColovrayGotteland, V
    Halazy, S
    SYNLETT, 1996, (06) : 507 - &
  • [10] One-pot synthesis of protected homoallyl amines
    Veenstra, S. J.
    Schmid, P.
    Tetrahedron Letters, 38 (06):