Synthesis of substituted benzo[b][1,4]oxazepine derivatives by the reaction of 2-aminophenols with alkynones

被引：10

作者：

Oshimoto, Kohei ^{[1
]}

Zhou, Biao ^{[1
]}

Tsuji, Hiroaki ^{[1
]}

Kawatsura, Motoi ^{[1
]}

机构：

[1] Nihon Univ, Coll Humanities & Sci, Dept Chem, Setagaya Ku, Tokyo 1568550, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 03期

基金：

日本学术振兴会;

关键词：

5-HT1A RECEPTOR AGONISTS; METAL-FREE SYNTHESIS; SMILES REARRANGEMENT; DIARYL ETHERIFICATION; HIGHLY-EFFICIENT; CYCLIZATION; UGI; DIBENZOXAZEPINONES; NITROGEN; PYRIDOBENZOXAZEPINONES;

D O I：

10.1039/c9ob02450f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a novel synthetic method accessing benzo[b][1,4]oxazepines that are one of the rare classes of benzoxazepine derivatives by reaction of 2-aminophenols with alkynones in 1,4-dioxane at 100 degrees C. A series of benzo[b][1,4]oxazepine derivatives can be prepared by using this synthetic protocol. Mechanistic experiments indicated that the hydroxy proton of the aminophenol could play a crucial role in the formation of an alkynylketimine intermediate that undergoes 7-endo-dig cyclization.

引用

页码：415 / 419

页数：5

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