Efficient one-pot synthesis of functionalised imidazo[1,2-a]pyridines and unexpected synthesis of novel tetracyclic derivatives by nucleophilic aromatic substitution†
Charles R. K.
Changunda, 
a
William K.
Mokone,
a
Amanda L.
Rousseau,
a
Dean
Brady,
a
Manuel A.
Fernandes
a
and
Moira L.
Bode
*a
a
William K.
Mokone,
a
Amanda L.
Rousseau,
a
Dean
Brady,
a
Manuel A.
Fernandes
a
and
Moira L.
Bode
*a
Abstract
Novel tetracyclic imidazo[1,2-a]pyridine derivatives have been prepared by intramolecular nucleophilic aromatic substitution of 5-fluoroimidazo[1,2-a]pyridines under basic conditions. Use of the non-nucleophilic alcoholic solvent tert-butanol, rather than methanol, increased the yield of the tetracycles by reducing the competing intermolecular reaction observed for methanol. In addition, a modified protocol for the dehydration of formamides to isocyanides has been found to be tolerant of an unprotected hydroxyl functional group and one-pot conversion to imidazo[1,2-a]pyridyl-aminocyclohexanol analogues is reported.
![Graphical abstract: Efficient one-pot synthesis of functionalised imidazo[1,2-a]pyridines and unexpected synthesis of novel tetracyclic derivatives by nucleophilic aromatic substitution](/en/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=C9RA10447J&imageInfo.ImageIdentifier.Year=2020)
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