Synthesis and Shuttling Behavior of [2]Rotaxanes with a Pyrrole Moiety

Yusuke Matsuoka; Yuichiro Mutoh; Isao Azumaya; Shoko Kikkawa; Takeshi Kasama; Shinichi Saito

doi:10.1021/acs.joc.5b02911

Synthesis and Shuttling Behavior of [2]Rotaxanes with a Pyrrole Moiety

J Org Chem. 2016 May 6;81(9):3479-87. doi: 10.1021/acs.joc.5b02911. Epub 2016 Mar 20.

Authors

Yusuke Matsuoka¹, Yuichiro Mutoh¹, Isao Azumaya², Shoko Kikkawa², Takeshi Kasama³, Shinichi Saito¹

Affiliations

¹ Department of Chemistry, Faculty of Science, Tokyo University of Science , Kagurazaka, Shinjuku, Tokyo 162-8601, Japan.
² Faculty of Pharmaceutical Sciences, Toho University , 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan.
³ Research Center for Medical and Dental Sciences, Tokyo Medical and Dental University , 1-5-45 Yushima, Bunkyo-ku, Tokyo 113-8510, Japan.

PMID: 26949996
DOI: 10.1021/acs.joc.5b02911

Abstract

We synthesized [2]rotaxanes with a pyrrole moiety from a [2]rotaxane with a 1,3-diynyl moiety. The conversion of the 1,3-diynyl moiety of the axle component to the pyrrole moiety was accomplished by a Cu-mediated cycloaddition of anilines. The cycloaddition reaction was accelerated when the [2]rotaxane was used as the substrate. The effect of the structure of the pyrrole moiety on the rate of the shuttling was studied.

Publication types

Research Support, Non-U.S. Gov't