微波促进由双丙二烯合成双环氮杂辛因-β-内酰胺

Microwave-promoted synthesis of bicyclic azocine-β-lactams from bis(allenes).

作者信息

Alcaide Benito, Almendros Pedro, Aragoncillo Cristina, Fernández Israel, Gómez-Campillos Gonzalo

机构信息

Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Quı́mica Orgánica I, Unidad Asociada al CSIC, Facultad de Quı́mica, Universidad Complutense de Madrid , 28040 Madrid, Spain.

出版信息

J Org Chem. 2014 Aug 1;79(15):7075-83. doi: 10.1021/jo501231q. Epub 2014 Jul 17.

DOI:10.1021/jo501231q

PMID:25010752

Abstract

A metal-free preparation of structurally novel bicyclic azocine-β-lactams has been developed. The first examples accounting for the preparation of eight-membered rings from bis(allenes) in the absence of metals have been achieved by the thermolysis of nonconjugated 2-azetidinone-tethered bis(allenes) on application of microwave irradiation. This selective carbocyclization reaction has been studied experimentally, and additionally, its mechanism has been investigated by a DFT study.

摘要

已开发出一种结构新颖的双环氮杂环辛烷-β-内酰胺的无金属制备方法。在微波辐射作用下，通过非共轭2-氮杂环丁酮连接的双烯丙基的热解，首次实现了在无金属条件下由双烯丙基制备八元环的实例。对该选择性碳环化反应进行了实验研究，此外，还通过密度泛函理论（DFT）研究对其机理进行了探究。