Synthesis of Bridged Tetrahydrobenzo[b]azepines and Derivatives through an Aza-Piancatelli Cyclization/Michael Addition Sequence

被引：50

作者：

Wang, Shengdong ^{[1
]}

Guillot, Regis ^{[1
]}

Carpentier, Jean-Francois ^{[2
]}

Sarazin, Yann ^{[2
]}

Bour, Christophe ^{[1
]}

Gandon, Vincent ^{[1
]}

Lebceuf, David ^{[1
]}

机构：

[1] Univ Paris Saclay, ICMMO, CNRS UMR 8182, Univ Paris Sud, Batiment 420, F-91405 Orsay, France

[2] Univ Rennes, CNRS UMR 6226, ISCR, F-35000 Rennes, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 03期

关键词：

electrocyclization; hexafluoroisopropanol; Lewis acid; medium-size N-heterocycles; tetrahydrobenzo[b]azepines; REARRANGEMENT; ALCOHOLS; INDOLES; ACCESS; POTENT;

D O I：

10.1002/anie.201911761

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report the preparation of bridged tetrahydrobenzo[b]azepines, which was accomplished through an aza-Piancatelli cyclization/Michael addition sequence in a one-pot fashion from readily available precursors. It is noteworthy that a general method to access these scaffolds was hitherto unprecedented. Additionally, the multifaceted aspects of this process have been exemplified through its application to the synthesis of 2-azabicyclo[3.2.1]octanes and bridged tetrahydrobenzo[b]oxepines, along with post-derivatizations.

引用

页码：1134 / 1138

页数：5

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