Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines via Two Tandem SNAr Events. Part 1-On the Importance of the Intermittent Smiles Rearrangement

被引：4

作者：

Sapegin, Alexander ^{[1
]}

Krasavin, Mikhail ^{[1
]}

机构：

[1] St Petersburg State Univ, St Petersburg 199034, Russia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 31-32期

基金：

俄罗斯科学基金会;

关键词：

Nucleophilic aromatic substitution; Smiles rearrangement; Oxazepines; Privileged structures; Synthons; CONSTRUCTION; DISCOVERY; STRATEGY;

D O I：

10.1002/ejoc.201900263

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New bis-nucleophilic precursors to [1.4]oxazepines synthesized via SNAr-Smiles rearrangement-SNAr cascade have been designed. Employing them in base-promoted condensation with aromatic bis-electrophiles allowed differentiating between highly and poorly reactive substrates (i.e. those which can and cannot pass through the Smiles rearrangement barrier, respectively). The reactivity toward the desired course of cyclization can be restored by introducing electron-withdrawing substituents in the bis-electrophile precursor. This strongly argues for the importance of the Smiles rearrangement for the successful overall ring formation.

引用

页码：5234 / 5241

页数：8

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