Issue 1, 2015

Polycyclic imidazo[1,2-a]pyridine analogs – synthesis via oxidative intramolecular C–H amination and optical properties

Abstract

A novel and straightforward approach to synthesize 5H-pyrido[2′,1′:2,3]imidazo[4,5-b]indoles has been developed. The key step is C–H amination of easily available 2-(2′-aminophenyl)imidazo[1,2-a]pyridines by the use of copper(II) triflate, trifluoroacetic acid and (diacetoxyiodo)benzene. The entire strategy consists of just four steps, starting from 2-aminopyridines and acetophenones, giving the target compounds in an overall yield of 20–35%. The optical properties of a library of π-expanded imidazo[1,2-a]pyridines were for the first time fully characterized, showing that these ladder-type compounds strongly absorb UV radiation and exhibit fluorescence in the 415–461 nm region.

Graphical abstract: Polycyclic imidazo[1,2-a]pyridine analogs – synthesis via oxidative intramolecular C–H amination and optical properties

Supplementary files

Article information

Article type
Research Article
Submitted
15 Sep 2014
Accepted
15 Oct 2014
First published
15 Oct 2014
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2015,2, 21-28

Author version available

Polycyclic imidazo[1,2-a]pyridine analogs – synthesis via oxidative intramolecular C–H amination and optical properties

Ł. Kielesiński, M. Tasior and D. T. Gryko, Org. Chem. Front., 2015, 2, 21 DOI: 10.1039/C4QO00248B

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