含钨乙烯基偶氮甲碱叶立德的分子间1,5-偶极环加成反应生成七元杂环。

Intermolecular 1,5-dipolar cycloaddition reaction of tungsten-containing vinylazomethine ylides leading to seven-membered heterocycles.

作者信息

Kusama Hiroyuki, Suzuki Yasuo, Takaya Jun, Iwasawa Nobuharu

机构信息

Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8551, Japan.

出版信息

Org Lett. 2006 Mar 2;8(5):895-7. doi: 10.1021/ol0529795.

DOI:10.1021/ol0529795

PMID:16494468

Abstract

Intermolecular 1,5-dipolar cycloaddition reaction of tungsten-containing vinylazomethine ylide, generated from o-(alk-3-en-1-ynyl)phenylbenzaldimines and tungsten carbonyl complex, with ketene acetals proceeds efficiently to give azepino[1,2-a]indole derivatives in good yield. Formation of [5+2] or [3+2] cycloadducts can be controlled by an appropriate choice of dipolarophile.

摘要

由邻（3-烯-1-炔基）苯基苯甲亚胺与羰基钨配合物生成的含钨乙烯基甲亚胺叶立德与乙烯酮缩醛的分子间1,5-偶极环加成反应能高效进行，以良好的产率得到氮杂环庚三烯并[1,2-a]吲哚衍生物。[5+2]或[3+2]环加成产物的形成可通过对偶极亲合体的适当选择来控制。