Synthesis of 5-alkyl-4-amino-2-(trifluoromethyl)pyridines and their transformation into trifluoromethylated 1H-pyrazolo[4,3-c]pyridines

被引:22
|
作者
Tyvorskii, VI
Bobrov, DN
Kulinkovich, OG
Tehrani, KA
De Kimpe, N
机构
[1] Belarusian State Univ, Dept Organ Chem, Minsk 220050, BELARUS
[2] Univ Ghent, Fac Agr & Appl Biol Sci, Dept Organ Chem, B-9000 Ghent, Belgium
关键词
4H-pyran-4-ones; 4-aminopyridines; 1H-pyrazolo[4,3-c]pyridines; Smiles rearrangement;
D O I
10.1016/S0040-4020(01)00024-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
5-Alkyl-4-amino-2-(trifluoromethyl)pyridines were prepared in good yields starting from the corresponding pyridinols either using condensation with tosyl isocyanate or by alkylation with 2-chloroacetamide and subsequent Smiles type rearrangement. The cyclisation of diazonium salts, generated from 5-alkyl-4-amino-2-(trifluoromethyl)pyridines afforded trifluoromethylated 1H-pyrazolo[4,3-c] pyri dines. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2051 / 2055
页数:5
相关论文
共 50 条
  • [31] (α-Fe2O3)-MCM-41 as a magnetically recoverable nanocatalyst for the synthesis of pyrazolo[4,3-c]pyridines at room temperature
    Rostamizadeh, Shahnaz
    Shadjou, Nasrin
    Azad, Mohammad
    Jalali, Nima
    [J]. CATALYSIS COMMUNICATIONS, 2012, 26 : 218 - 224
  • [32] A mild synthesis of [1,2,4]triazolo[4,3-a]pyridines
    Schmidt, Michael A.
    Qian, Xinhua
    [J]. TETRAHEDRON LETTERS, 2013, 54 (42) : 5721 - 5726
  • [33] Palladium-Catalyzed Synthesis of 1H-Pyrazolo[4,3-c]quinolines and 4-Anilinoquinoline-3-carbonitriles from 4-Chloroquinoline-3-carbaldehydes
    Wang, Chao
    Tang, Caifei
    Li, Zhiming
    Wang, Quanrui
    [J]. SYNTHESIS-STUTTGART, 2015, 47 (20): : 3139 - 3146
  • [34] N-Boc-4-aminopyrazole-5-carbaldehydes in Friendländer synthesis of pyrazolo[4,3-b]pyridines
    Georgiy G. Yakovenko
    Oleh A. Lukianov
    Andriy V. Bol’but
    Mykhailo V. Vovk
    [J]. Chemistry of Heterocyclic Compounds, 2019, 55 : 379 - 385
  • [35] New access to the 1H-pyrazolo[4,3-c]pyridine core from bis-acetylenic-N-benzoylhydrazones
    Commeiras, L
    Woodcock, SC
    Baldwin, JE
    Adlington, RM
    Cowley, AR
    Wilkinson, PJ
    [J]. TETRAHEDRON, 2004, 60 (04) : 933 - 938
  • [36] PREPARATION AND REACTIONS OF PYRAZOLO[4,3-C]-PYRIDIN-4(5H)-ONES
    MAREI, MG
    [J]. AFINIDAD, 1993, 50 (443) : 55 - 58
  • [37] Syntheses and biological properties of pyrazolo[4,3-c]triazolo[4,3-a][1,5]benzodiazepines
    Ahabchane, NH
    Ibrahimi, S
    Salem, M
    Essassi, EM
    Amzazi, S
    Benjouad, A
    [J]. COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II FASCICULE C-CHIMIE, 2001, 4 (12): : 917 - 924
  • [38] A new strategy for the synthesis of pyrazolo[4,3-e][1,2,4]triazolo[4,3-c]pyrimidines and pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidines
    Shawali, Ahmad Sami
    Hassaneen, Hamdi M.
    Shurrab, Nabil Kh.
    [J]. TETRAHEDRON, 2008, 64 (45) : 10339 - 10343
  • [39] SYNTHESIS AND PROPERTIES OF 5-ALKYL-2-(4-CYANOPHENYL)PYRIDINES
    GREBYONKIN, MF
    PETROV, VF
    BELYAEV, VV
    PAVLUCHENKO, AI
    SMIRNOVA, NI
    KOVSHEV, EI
    TITOV, VV
    IVASHCHENKO, AV
    [J]. MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1985, 129 (1-3): : 245 - 257
  • [40] SYNTHESIS OF 2,4,5-TRIARYL-5H-CHROMENO[4,3-b]PYRIDINES IN IONIC LIQUID
    Wu, Hui
    Wan, Yu
    Chen, Xiu-mei
    Lu, Lei-lei
    Shen, Yang
    Chen, Cai-fa
    Xin, Hai-qiang
    Xu, Hua-hong
    Pang, Li-ling
    Ma, Rui
    Yue, Cai-hui
    [J]. HETEROCYCLES, 2009, 78 (02) : 357 - 367