Regioselective synthesis of the 4,5-dialkoxy-2-nitroanilines bearing two different alkoxy substituents

被引：3

作者：

Grolik, Jaroslaw ^{[1
]}

Reka, Pawel ^{[1
]}

Gorczyca, Magdalena ^{[1
]}

Stadnicka, Katarzyna ^{[1
]}

机构：

[1] Jagiellonian Univ, Fac Chem, ul Gronostajowa 2, PL-30387 Krakow, Poland

来源：

TETRAHEDRON LETTERS | 2022年 / 99卷

关键词：

Aromatic nucleophilic substitution; 2-nitroaniline; Regioselectivity; Chemoselectivity; Transetherification; SKRAUP REACTION; ANTIMALARIAL;

D O I：

10.1016/j.tetlet.2022.153830

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This article reports the regioselective and chemoselective synthesis of 4,5-dialkoxy-2-nitroanilines substituted with two alkoxys at C-4 and C-5. Here we show the optimization protocol of the transetherification reaction used to synthesize 20 new compounds with good to excellent yields (50-92%). We describe a simple and efficient one-step procedure that can be applied to obtain a significant number of pharmacologically active compounds, including antimalarial drug Primaquine analogs. (c) 2022 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

引用

页数：7

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