Solid phase synthesis of 1,3,5-trisubstituted pyridin-2-ones

被引：12
|
作者：
Linn, JA [1 ]
Gerritz, SW [1 ]
Handlon, AL [1 ]
Hyman, CE [1 ]
Heyer, D [1 ]
机构：
[1] Glaxo Wellcome Res & Dev Ltd, Res Triangle Pk, NC 27709 USA
来源：
TETRAHEDRON LETTERS | 1999年 / 40卷 / 12期
关键词：
D O I：
10.1016/S0040-4039(98)02628-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The solid phase synthesis of 1,3,5-trisubsituted pyridin-2-ones is reported via selective (NH)-N-1- alkylation of 3-amino-5-carbomethoxy-1H-pyridin-2-one with a solid-supported halo-acid. Coupling of an acid to solid-supported 3-aminopyridinone was followed by saponification of the methyl ester to give the acid. Activation of the acid via the pentafluorophenyl ester allowed reaction with an amine, and cleavage from the solid support with TFA:H2O (95:5) provided 1,3,5-trisubstituted pyridin-2-ones. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2227 / 2230
页数：4
相关论文
共 50 条
  • [31] Synthesis of 1,3,5-trisubstituted pyrazolines as potential antimalarial and antimicrobial agents
    Mishra, Vikash K.
    Mishra, Mitali
    Kashaw, Varsha
    Kashaw, Sushil K.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (06) : 1949 - 1962
  • [32] SYNTHESIS OF NOVEL 1,3,5-TRISUBSTITUTED PYRAZOLES AS POTENTIAL HYPOGLYCEMIC AGENTS
    MOKHTAR, HM
    ELKHAWASS, SM
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1988, 35 (01) : 57 - 62
  • [33] Vinylogous Blaise Reaction: Conceptually New Synthesis of Pyridin-2-ones
    Rao, H. Surya Prakash
    Muthanna, Nandurka
    Padder, Ashiq Hussain
    SYNLETT, 2018, 29 (12) : 1649 - 1653
  • [34] Solid-phase synthesis of 1,2,5-trisubstituted 4-imidazolidinones
    Rinnová, M
    Vidal, AS
    Nefzi, A
    Houghten, RA
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (03): : 209 - 213
  • [35] Synthesis of 1- and 3-substituted imidazo[4,5-b]pyridin-2-ones
    Yutilov, Yu. M.
    Smolyar, N. N.
    Lomov, A. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (06) : 897 - 900
  • [36] Design and synthesis of 1,3,5-trisubstituted 1,2,4-triazoles as CYP enzyme inhibitors
    Al-Soud, Yaseen A.
    Heydel, Michael
    Hartmann, Rolf W.
    TETRAHEDRON LETTERS, 2011, 52 (48) : 6372 - 6375
  • [37] One-pot parallel synthesis of 1,3,5-trisubstituted 1,2,4-triazoles
    Dmytro S. Radchenko
    Vasyl S. Naumchyk
    Igor Dziuba
    Andrii A. Kyrylchuk
    Kateryna E. Gubina
    Yurii S. Moroz
    Oleksandr O. Grygorenko
    Molecular Diversity, 2022, 26 : 993 - 1004
  • [38] Synthesis and Biological Activity of Novel 1,3,5-Trisubstituted 1,2,4-Triazole Derivatives
    Parmar, Kokila
    Suthar, Bharat
    Prajapati, Saraju
    Suthar, Arun
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (01) : 156 - 161
  • [39] One-pot parallel synthesis of 1,3,5-trisubstituted 1,2,4-triazoles
    Radchenko, Dmytro S.
    Naumchyk, Vasyl S.
    Dziuba, Igor
    Kyrylchuk, Andrii A.
    Gubina, Kateryna E.
    Moroz, Yurii S.
    Grygorenko, Oleksandr O.
    MOLECULAR DIVERSITY, 2022, 26 (02) : 993 - 1004
  • [40] Synthesis and analgesic activity of 1,3,5-trisubstituted pyrazoles containing a diterpenoid moiety
    M. E. Mironov
    A. I. Poltanovich
    T. V. Rybalova
    M. P. Dolgikh
    T. G. Tolstikova
    E. E. Shults
    Russian Chemical Bulletin, 2020, 69 : 537 - 546
12345