Novel synthesis of 2,3-dihydrobenzofuran-3-amines from salicylic aldehydes: Trimethylsilyl as traceless activating group

被引：2

作者：

Khardina, Polina A. ^{[1
]}

Buev, Evgeny M. ^{[1
]}

Moshkin, Vladimir S. ^{[1
]}

Sosnovskikh, Vyacheslav Y. ^{[1
]}

机构：

[1] Ural Fed Univ, Inst Nat Sci & Math, Ekaterinburg 620000, Russia

来源：

TETRAHEDRON LETTERS | 2024年 / 139卷

基金：

俄罗斯科学基金会;

关键词：

2,3-Dihydrobenzofurans; Cesium fluoride; Traceless activating group; Salicylic aldehydes; Trimethylsilanes; CARBOXYLIC-ACIDS; PHOTOREDOX;

D O I：

10.1016/j.tetlet.2024.154992

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Salicylic aldehydes were readily alkylated with (chloromethyl)trimethylsilane to give silylated ortho-methoxy benzaldehydes in 85-96 % yields. These aldehydes were converted into alkyl and aryl imines in excellent yields. O-(Trimethylsilyl)methyl moiety was applied as the synthetic equivalent of aryloxymethyl anion in the nucleophilic cyclization at the imine group promoted by CsF in DMF at 140 degrees C. Using this traceless methodology, 2,3dihydrobenzofuran-3-amines were synthesized from salicylic aldehydes in 25-55 % yields in three steps.

引用

页数：4

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