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Issue 1, 2015
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Polycyclic imidazo[1,2-a]pyridine analogs – synthesis via oxidative intramolecular C–H amination and optical properties

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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

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The article was received on 15 Sep 2014, accepted on 15 Oct 2014 and first published on 15 Oct 2014


Article type: Research Article
DOI: 10.1039/C4QO00248B
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Org. Chem. Front., 2015,2, 21-28
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    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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