Copper(II) chloride promoted transformation of amines into guanidines and asymmetrical N,N′-disubstituted guanidines

被引：18
|
作者：
Kelly, Brendan [1 ]
Rozas, Isabel [1 ]
机构：
[1] Univ Dublin Trinity Coll, Sch Chem, Trinity Biomed Sci Inst, Dublin 2, Ireland
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 30期
关键词：
Guanidine; Copper chloride; N; N'-Disubstituted guanidine; 2-Aminoimidazoline; 2-AMINOIMIDAZOLINE AROMATIC DERIVATIVES; ALPHA(2)-ADRENOCEPTOR ANTAGONISTS; GUANYLATION; REAGENT;
D O I：
10.1016/j.tetlet.2013.05.070
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We present a concise, less-toxic and broadly applicable method for coupling weakly nucleophilic amines with N,N'-di-(tert-butoxycarbonyl)thiourea, N-(tert-butxoycarbonyl), N'-alkyl/arylsubstituted-thioureas and N,N'-di-(tert-butoxycarbonyl)imidazolidine-2-thione in the presence of copper(II) chloride. Subsequent removal of Boc protecting groups affords guanidines, di-substituted guanidines and 2-aminoimidazolines in modest to excellent overall yields. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3982 / 3984
页数：3
相关论文
共 50 条
  • [41] Direct synthesis of bicyclic guanidines through unprecedented palladium(II) catalysed diamination with copper chloride as oxidant
    Hovelmann, Claas H.
    Streuff, Jan
    Brelot, Lydia
    Muniz, Kilian
    CHEMICAL COMMUNICATIONS, 2008, (20) : 2334 - 2336
  • [42] One-Pot Synthesis of C 2 Symmetric and Asymmetric N,N,N-Substituted Guanidines from Aryl Isothiocyanates and Amines
    Wangngae, Sirilak
    Pattarawarapan, Mookda
    Phakhodee, Wong
    SYNLETT, 2016, 27 (07) : 1121 - 1127
  • [43] Aluminum chloride: A highly efficient catalyst for addition of amines to carbodiimides to synthesize substituted guanidines
    Zhu XueHua
    Xu Fan
    Shen Qi
    CHINESE SCIENCE BULLETIN, 2012, 57 (26): : 3419 - 3422
  • [44] Aluminum chloride:A highly efficient catalyst for addition of amines to carbodiimides to synthesize substituted guanidines
    ZHU XueHua 1
    2 State Key Laboratory of Organometallic Chemistry
    ChineseScienceBulletin, 2012, 57 (26) : 3419 - 3422
  • [45] PREDICTION OF TAUTOMERIC EQUILIBRIA FOR N,N,N',N''-TETRA-SUBSTITUTED AND N,N,N'-TRISUBSTITUTED GUANIDINES
    RACZYNSKA, ED
    JOURNAL OF CHEMICAL RESEARCH-S, 1988, (08): : 258 - 259
  • [46] Orthoamides LXVIII: N,N′,N"-Peralkylated Guanidinium Salts by Alkylation of N,N,N′,N′,N"-Pentasubstituted Guanidines
    Kantlehner, Willi
    Edelmann, Kai
    Gissel, Alexander
    Scherr, Oliver
    Vetter, Jens
    Wezstein, Markus
    Ziegler, Georg
    Mezger, J.
    Iliev, Boyan
    ACTA CHIMICA SLOVENICA, 2009, 56 (03) : 612 - 621
  • [47] A novel facile solid-phase strategy for the synthesis of N,N′,N"-substituted guanidines
    Kilburn, JP
    Lau, J
    Jones, RCF
    TETRAHEDRON, 2002, 58 (09) : 1739 - 1743
  • [48] Orthoamides by selective borohydride reduction of N,N′,N"-triacyl- and N,N′,N"-tri(alkoxycarbonyl)-guanidines
    Davis, Matthew C.
    Groshens, Thomas J.
    TETRAHEDRON LETTERS, 2019, 60 (05) : 427 - 431
  • [49] DISTRIBUTION OF GUANIDINES, PHOSPHAGENS AND N-AMIDINO PHOSPHOKINASES IN ECHINOIDS
    GRIFFITHS, DE
    MORRISON, JF
    ENNOR, AH
    BIOCHEMICAL JOURNAL, 1957, 65 (04) : 612 - 617
  • [50] Radical Synthesis of Guanidines from N-Acyl Cyanamides
    Larraufie, Marie-Helene
    Ollivier, Cyril
    Fensterbank, Louis
    Malacria, Max
    Lacote, Emmanuel
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (12) : 2178 - 2181
12345