通过末端炔烃的三乙炔基吡啶的氧化偶联制备乙炔基吡啶大环。

Preparation of ethynylpyridine macrocycles by oxidative coupling of an ethynylpyridine trimer with terminal acetylenes.

机构信息

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

出版信息

J Org Chem. 2011 Jan 7;76(1):309-11. doi: 10.1021/jo101921e. Epub 2010 Dec 8.

DOI:10.1021/jo101921e

Abstract

Macrocycles consisted of pyridine rings and acetylene bonds were prepared by Eglinton coupling from a tandem precursor bearing two terminal alkynyl groups. The composition of molecular size in the cyclized products changed by the reaction solvent. In pyridine, 9-meric and bigger macrocycles were obtained, while that of 6-mer was not. On the other hand, in pyridine/THF mixed solvent, the 6-mer was obtained as a major product.

摘要

大环化合物由吡啶环和乙炔键组成，是通过带有两个末端炔基的串联前体的 Eglinton 偶联制备的。环化产物中分子大小的组成随反应溶剂而变化。在吡啶中，得到了 9 聚体及更大的大环化合物，而 6 聚体则没有。另一方面，在吡啶/THF 混合溶剂中，主要得到 6 聚体。