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
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 30期
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
  • [41] One-Pot Synthesis of O-Aryl Carbamates
    Varjosaari, Sami E.
    Suating, Paolo
    Adler, Marc J.
    SYNTHESIS-STUTTGART, 2016, 48 (01): : 43 - 47
  • [42] One-pot asymmetric synthesis of either diastereomer of tert-butanesulfinyl-protected amines from ketones
    Tanuwidjaja, Jessica
    Peltier, Hillary M.
    Ellman, Jonathan A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
  • [43] One-pot asymmetric synthesis of either diastereomer of tert-butanesulfinyl-protected amines from ketones
    Tanuwidjaja, Jessica
    Peltier, Hillary M.
    Ellman, Jonathan A.
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (02): : 626 - 629
  • [44] One-pot synthesis of unsymmetrical triarylamines from aniline precursors.
    Buchwald, SL
    Harris, MC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U196 - U196
  • [45] Pd(II)/Ag(I)-Promoted One-Pot Synthesis of Cyclic Ureas from (Hetero)Aromatic Amines and Isocyanates
    Youn, So Won
    Kim, Yi Hyun
    ORGANIC LETTERS, 2016, 18 (23) : 6140 - 6143
  • [46] One-pot chemoenzymatic synthesis of protected cyanohydrins
    Purkarthofer, T
    Skranc, W
    Weber, H
    Griengl, H
    Wubbolts, M
    Scholz, G
    Pöchlauer, P
    TETRAHEDRON, 2004, 60 (03) : 735 - 739
  • [47] A novel one-pot synthesis of unsymmetrical acyclic imides
    Habibi, Zohreh
    Salehi, Peyman
    Zolfigol, Mohammad Ali
    Yousefi, Maryam
    SYNLETT, 2007, (05) : 812 - 814
  • [48] A facile and one-pot synthesis of Nα-Fmoc/Bsmoc/Boc/Z-protected ureidopeptides and peptidyl ureas employing diphenylphosphoryl azide [DPPA]
    Sureshbabu, Vommina V.
    Chennakrishnareddy, G.
    Narendra, N.
    TETRAHEDRON LETTERS, 2008, 49 (08) : 1408 - 1412
  • [49] A convenient, one-pot synthesis of thiocarbamates using bis(trichloromethyl) carbonate
    Su, W. K.
    Zhang, J. P.
    Liang, X. R.
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2006, 38 (04) : 404 - 410
  • [50] Efficient one-pot synthesis of unsymmetrical cysteine disulfides
    Hunter, Roger
    Stellenboom, Nashia
    Caira, Mino R.
    SYNLETT, 2008, (02) : 252 - 254
12345