A simple one-pot synthesis of triflyl guanidines: access to highly substituted electron-poor guanidines

被引:8
|
作者
Thai, Karen [1 ]
Clement, Craig W. [1 ]
Gravel, Michel [1 ]
机构
[1] Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
基金
加拿大自然科学与工程研究理事会; 加拿大创新基金会;
关键词
Guanidines; Isothiocyanates; Trifluoromethanesulfonamide; Regioselective alkylation;
D O I
10.1016/j.tetlet.2009.09.040
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Unsymmetrical di- and trisubstituted triflyl guanidines are accessed through a simple, one-pot protocol from the corresponding isothiocyanate and amine. Furthermore, in the presence of base, trisubstituted triflyl guanidines are alkylated to obtain tetrasubstituted triflyl guanidines in high yields and complete regioselectivity (C) 2009 Elsevier Ltd. All rights reserved
引用
收藏
页码:6540 / 6542
页数:3
相关论文
共 50 条
  • [1] One-pot synthesis of n-alkyl substituted phosphoryl guanidines
    de Souza, MC
    de Macedo, WP
    da Silva, MCM
    Ramos, GCD
    Alt, HG
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2004, 179 (06) : 1047 - 1054
  • [2] A facile and practical one-pot 'catch and release' synthesis of substituted guanidines
    Wang, Ying
    Sauer, Daryl R.
    Djuric, Stevan W.
    TETRAHEDRON LETTERS, 2009, 50 (36) : 5145 - 5148
  • [3] A versatile one-pot synthesis of 1,3-substituted guanidines from carbamoyl isothiocyanates
    Linton, BR
    Carr, AJ
    Orner, BP
    Hamilton, AD
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05): : 1566 - 1568
  • [4] Design, synthesis, and application of chiral electron-poor guanidines as hydrogen-bonding catalysts for the Michael reaction
    Thai, Karen
    Gravel, Michel
    TETRAHEDRON-ASYMMETRY, 2010, 21 (06) : 751 - 755
  • [5] SYNTHETIC APPLICATIONS OF BIS(IMINOPHOSPHORANES) - ONE-POT PREPARATION OF CYCLIC GUANIDINES
    MOLINA, P
    ALAJARIN, M
    VIDAL, A
    ANALES DE QUIMICA, 1993, 89 (01): : 137 - 138
  • [6] One-pot synthesis of highly substituted indolines
    Liu, Kevin G.
    Lo, Jennifer R.
    Robichaud, Albert J.
    TETRAHEDRON, 2010, 66 (03) : 573 - 577
  • [7] Application of α-chloroaldoxime O-methanesulfonates to one-pot synthesis of N,N′,N"-substituted guanidines via Tiemann rearrangement
    Yamamoto, Yuhei
    Mizuno, Hiroo
    Tsuritani, Takayuki
    Mase, Toshiaki
    TETRAHEDRON LETTERS, 2009, 50 (42) : 5813 - 5815
  • [8] One-pot synthesis of diverse N,N′-disubstituted guanidines from N-chlorophthalimide, isocyanides and amines via N-phthaloyl-guanidines
    Demjen, Andras
    Angyal, Aniko
    Wolfling, Janos
    Puskas, Laszlo G.
    Kanizsai, Ivan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (12) : 2143 - 2149
  • [9] SYNTHETIC APPLICATIONS OF BIS(IMINOPHOSPHORANES) - ONE-POT PREPARATION OF RIGID BICYCLIC GUANIDINES
    MOLINA, P
    ALAJARIN, M
    VIDAL, A
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07): : 1687 - 1695
  • [10] 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