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通过涉及重氮亚甲基化合物净插入的4π-8π串联电环化反应，将苯并环丁烯酮轻松转化为2,3-苯并二氮杂卓。

Facile transformation of benzocyclobutenones into 2,3-benzodiazepines via 4pi-8pi tandem electrocyclic reactions involving net insertion of diazomethylene compounds.

作者信息

Matsuya Yuji, Ohsawa Noriko, Nemoto Hideo

机构信息

Faculty of Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.

出版信息

J Am Chem Soc. 2006 Oct 11;128(40):13072-3. doi: 10.1021/ja065277z.

DOI:10.1021/ja065277z
PMID:17017785
Abstract

Efficient transformations of benzocyclobutenones into 2,3-benzodiazepines by a formal insertion of diazomethylene compounds are described. This sequential process includes nucleophilic addition of diazomethylene anion, oxy-anion accelerated o-quinodimethane formation by an electrocyclic ring-opening reaction, and 8pi-electrocyclization in one-pot under remarkably mild conditions. Intermediary oxy-anion plays an important role for the efficient transformations.

摘要

描述了通过重氮亚甲基化合物的形式插入将苯并环丁烯酮高效转化为2,3-苯并二氮杂卓的方法。这一连续过程包括重氮亚甲基阴离子的亲核加成、通过电环化开环反应由氧阴离子加速邻醌二甲烷的形成以及在非常温和的条件下一锅法进行的8π-电环化反应。中间的氧阴离子对高效转化起着重要作用。

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