Solid-phase synthesis of benzazoles, quinazolines, and quinazolinones using an alkoxyamine linker

被引:7
|
作者
Yamaguchi, Kota [1 ]
Noda, Takeshi [2 ]
Higuchi, Yusuke [1 ]
Aoki, Naoyuki [1 ]
Yamaguchi, Rika [1 ]
Kubo, Miwa [3 ]
Harada, Kenichi [3 ]
Fukuyama, Yoshiyasu [3 ]
Hioki, Hideaki [1 ]
机构
[1] Gunma Univ, Fac Educ, Maebashi, Gunma 3718510, Japan
[2] Kanagawa Inst Technol, Dept Appl Biosci, Atsugi, Kanagawa 2430292, Japan
[3] Tokushima Bunri Univ, Fac Pharmaceut Sci, Yamashiro, Tokushima 7708514, Japan
关键词
Solid-phase synthesis; Alkoxyamine Linker; Benzimidazole; Quinazoline; Quinazolinone; COMBINATORIAL SYNTHESIS; SINGLE-LAYER; BENZOTHIAZOLES; HETEROCYCLES; OLEDS; HOSTS; BLUE;
D O I
10.1016/j.tetlet.2014.08.095
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An alkoxyamine linker was applied for the solid-phase synthesis of benzazoles, quinazolines, and quinazolinones. Aromatic aldehydes were anchored by aldoxime linkage. After some reactions on a solid support, the products were cleaved with paraformaldehyde under the acidic conditions to afford the corresponding aldehydes, which were subsequently subjected to oxidative coupling with 2-substituted anilines under air atmosphere to give the desired compounds. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5793 / 5797
页数:5
相关论文
共 50 条
  • [1] Solid-phase synthesis of benzothiazoles using an alkoxyamine linker
    Hioki, Hideaki
    Matsushita, Kimihito
    Noda, Takeshi
    Yamaguchi, Kota
    Kubo, Miwa
    Harada, Kenichi
    Fukuyama, Yoshiyasu
    TETRAHEDRON LETTERS, 2012, 53 (33) : 4337 - 4342
  • [2] Solid-Phase Friedlander Synthesis Using an Alkoxyamine Linker
    Yamaguchi, Kota
    Noda, Takeshi
    Tomizawa, Toshiki
    Kanai, Eriko
    Hioki, Hideaki
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (22) : 4990 - 4995
  • [3] Traceless Solid-Phase Synthesis of Trisubstituted Quinazolines
    Fueloepova, Veronika
    Cziesla, Lauren
    Fleming, Megan
    Lu, Yiwei
    Voelker, Adrienne
    Krchnak, Viktor
    ACS COMBINATORIAL SCIENCE, 2015, 17 (08) : 470 - 473
  • [4] A decarboxylative traceless linker approach for the solid phase synthesis of quinazolines
    Cobb, JM
    Fiorini, MT
    Goddard, CR
    Theoclitou, ME
    Abell, C
    TETRAHEDRON LETTERS, 1999, 40 (05) : 1045 - 1048
  • [5] Solid-phase synthesis of hydroxysteroid derivatives using the diethylsilyloxy linker
    Maltais, R
    Tremblay, MR
    Poirier, D
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2000, 2 (06): : 604 - 614
  • [6] Solid-phase synthesis of peptide aminoalkylamides using an allyl linker
    Kaljuste, K
    Unden, A
    TETRAHEDRON LETTERS, 1996, 37 (17) : 3031 - 3034
  • [7] Novel Alkoxyamine Linker to Load Ketones for Solid-Phase Synthesis: Application of the Synthesis of 1,4-Benzodiazepine-2-ones
    Matsushita, Kimihito
    Okamoto, Chieko
    Yoshimoto, Mayumi
    Harada, Kenichi
    Kubo, Miwa
    Fukuyama, Yoshiyasu
    Hioki, Hideaki
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (03): : 311 - 314
  • [8] Solid-phase synthesis of 4-substituted quinazolines
    Matlamela, Lerato N.
    Bose, Nripendra K.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [9] A nonacid degradable linker for solid-phase synthesis
    Colombo, Aina
    De la Figuera, Natalia
    Fernandez, Joan Carles
    Fernandez-Forner, Dolors
    Albericio, Fernando
    Forns, Pilar
    ORGANIC LETTERS, 2007, 9 (21) : 4319 - 4322
  • [10] Novel linker for the solid-phase synthesis of guanidines
    Josey, JA
    Tarlton, CA
    Payne, CE
    TETRAHEDRON LETTERS, 1998, 39 (33) : 5899 - 5902