氮杂三喹烷：合成、结构与反应活性

Azatriquinanes: Synthesis, Structure, and Reactivity.

作者信息

Hext Nicholas M., Hansen Jens, Blake Alexander J., Hibbs David E., Hursthouse Michael B., Shishkin Oleg V., Mascal Mark

机构信息

Department of Chemistry, University of Nottingham, Nottingham NG7 2RD, U.K., and Department of Chemistry, University of Wales Cardiff, P.O. Box 912, Cardiff CF1 3TB, U.K.

出版信息

J Org Chem. 1998 Aug 21;63(17):6016-6020. doi: 10.1021/jo980788s.

DOI:10.1021/jo980788s

PMID:11672206

Abstract

Azatriquinane, a tricyclic amine with rigid, hemispherical topology, is synthesized in six steps from pyrrole. This first example of a [2.2.2]cyclazine can be oxidatively dimerized to a novel, highly strained heptacycle or oxidized with chlorine to give an azatriquinacene, a theoretical precursor to diazadodecahedrane via Woodward dimerization.

摘要

氮杂三环癸烷是一种具有刚性半球形拓扑结构的三环胺，由吡咯经六步合成。这种[2.2.2]环嗪的首个实例可被氧化二聚为一种新型的、高度张力的七元环，或用氯氧化得到氮杂三环癸三烯，它是通过伍德沃德二聚反应生成二氮杂十二面体烷的理论前体。