A simple solid-phase synthesis of disubstituted guanidines using Rink amide resin as an amine component

被引：22
|
作者：
Li, M [1 ]
Wilson, LJ [1 ]
Portlock, DE [1 ]
机构：
[1] Procter & Gamble Pharmaceut, Hlth Care Res Ctr, Mason, OH 45040 USA
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 12期
关键词：
disubstituted guanidines; solid-phase synthesis; Rink amide resin;
D O I：
10.1016/S0040-4039(01)00162-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A practical solid-phase synthesis that simply uses Rink amide resin as an amine component in reacting with aromatic isothiocyanates and aliphatic amines to generate disubstituted guanidines is described. No special linker or guanylation reagents are involved in this method. The product is obtained in a 'traceless-linker' fashion and in high yield and purity when an electron-deficient isothiocyanate is employed. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2273 / 2275
页数：3
相关论文
共 50 条
  • [1] Solid-phase synthesis of disubstituted guanidines
    Kearney, PC
    Fernandez, M
    Flygare, JA
    TETRAHEDRON LETTERS, 1998, 39 (18) : 2663 - 2666
  • [2] Solid-phase synthesis of disubstituted guanidines utilizing a novel isothiocyanate resin.
    Wilson, LJ
    Li, M
    Klopfenstein, SR
    Yun, YK
    Burt, T
    Morand, K
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U120 - U120
  • [3] Modular three-component solid-phase synthesis of unsymmetrical guanidines via resin capture of carbodiimides
    Boguszewski, PA
    Rahman, SS
    Ganesan, A
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (01): : 32 - 34
  • [4] A convenient solid phase synthesis of disubstituted guanidines
    Sandanayake, S
    Perera, S
    Ede, NJ
    QSAR & COMBINATORIAL SCIENCE, 2004, 23 (08): : 655 - 661
  • [5] To Rink or Not to Rink Amide Link, that is the Question to Address for More Economical and Environmentally Sound Solid-Phase Peptide Synthesis
    Tarek Kassem
    David Sabatino
    Xin Jia
    X. X. Zhu
    William D. Lubell
    International Journal of Peptide Research and Therapeutics, 2009, 15 : 211 - 218
  • [6] To Rink or Not to Rink Amide Link, that is the Question to Address for More Economical and Environmentally Sound Solid-Phase Peptide Synthesis
    Kassem, Tarek
    Sabatino, David
    Jia, Xin
    Zhu, X. X.
    Lubell, William D.
    INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS, 2009, 15 (03) : 211 - 218
  • [7] Solid-phase synthesis of trisubsituted guanidines
    Hopkins, TP
    Dener, JM
    Boldi, AM
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (02): : 167 - 174
  • [8] Solid-phase synthesis of trisubstituted guanidines
    Drewry, DH
    Gerritz, SW
    Linn, JA
    TETRAHEDRON LETTERS, 1997, 38 (19) : 3377 - 3380
  • [9] Solid-phase synthesis of N-acyl-N′-alkyl/aryl disubstituted guanidines
    Ghosh, JK
    Hol, WGJ
    Fan, EK
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (06): : 2161 - 2164
  • [10] Novel linker for the solid-phase synthesis of guanidines
    Josey, JA
    Tarlton, CA
    Payne, CE
    TETRAHEDRON LETTERS, 1998, 39 (33) : 5899 - 5902
12345