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

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 42期

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

页码：5793 / 5797

页数：5

共 50 条

[41] A Dde-based carboxy linker for solid-phase synthesis
Chhabra, SR
Parekh, H
Khan, AN
Bycroft, BW
Kellam, B
TETRAHEDRON LETTERS, 2001, 42 (11) : 2189 - 2192
[42] A SILICON-BASED LINKER FOR TRACELESS SOLID-PHASE SYNTHESIS
PLUNKETT, MJ
ELLMAN, JA
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19): : 6006 - 6007
[43] A simple oxazolidine linker for solid-phase synthesis of peptide aldehydes
Kang, Wu
Wang, Weiguo
Zhi, XiaoXia
Zhang, Bo
Wei, Ping
Xu, HongYan
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (02) : 1187 - 1188
[44] Acetophenone-based linker for solid-phase peptide synthesis
Bui, CT
Bray, AM
Nguyen, T
Ercole, F
Rasoul, F
Sampson, W
Maeji, NJ
JOURNAL OF PEPTIDE SCIENCE, 2000, 6 (02) : 49 - 56
[45] A new versatile linker for the solid-phase synthesis of secondary amines
Glatz, H
Bannwarth, W
TETRAHEDRON LETTERS, 2003, 44 (01) : 149 - 152
[46] Silicon-based linker for traceless solid-phase synthesis
Plunkett, Matthew J.
Ellman, Jonathan A.
Journal of Organic Chemistry, 1995, 60 (19):
[47] An oxidation-labile traceless linker for solid-phase synthesis
Stieber, F
Grether, U
Waldmann, H
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (08) : 1073 - 1077
[48] An alkanesulfonamide "safety-catch" linker for solid-phase synthesis
Backes, BJ
Ellman, JA
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07): : 2322 - 2330
[49] A Photolabile Linker for the Solid-Phase Synthesis of Peptide Hydrazides and Heterocycles
Qvortrup, Katrine
Komnatnyy, Vitaly V.
Nielsen, Thomas E.
ORGANIC LETTERS, 2014, 16 (18) : 4782 - 4785
[50] A new vinyl ether type linker for solid-phase synthesis
Yoo, S
Gong, YD
Choi, MY
Seo, J
Yi, KY
TETRAHEDRON LETTERS, 2000, 41 (33) : 6415 - 6418

← 1 2 3 4 5 →