A collection of 2‐aryl‐3‐vinylimidazo[1,2‐a]pyridines, substituted on the pyridine ring and/or the aryl substituent, can be obtained by reaction of 2‐aminopyridines with properly substituted nitrobutadienes, originated by an initial ring opening of a nitrothiophenic precursor. Although the aza‐Michael addition of 2‐aminopyridine on a nitrovinyl moiety is the starting point of classic approaches to imidazopyridines, the final structures generated herein are the result of a cascade process made possible by the particular functionalization on the conjugated systems. Beside the general interest inherent to the pharmacologically versatile imidazo[1,2‐a]pyridine structural motif, the substituents present in the obtained compounds allow specific synthetic elaboration to e. g. polycyclic fluorescent heterocycles.

2‐Aryl‐3‐Vinyl Substituted Imidazo[1,2‐a]pyridines and Fluorescent Electrocyclization Derivatives therefrom

Alice Benzi;Lara Bianchi;Massimo Maccagno;Giovanni Petrillo;Cinzia Tavani
2020

Abstract

A collection of 2‐aryl‐3‐vinylimidazo[1,2‐a]pyridines, substituted on the pyridine ring and/or the aryl substituent, can be obtained by reaction of 2‐aminopyridines with properly substituted nitrobutadienes, originated by an initial ring opening of a nitrothiophenic precursor. Although the aza‐Michael addition of 2‐aminopyridine on a nitrovinyl moiety is the starting point of classic approaches to imidazopyridines, the final structures generated herein are the result of a cascade process made possible by the particular functionalization on the conjugated systems. Beside the general interest inherent to the pharmacologically versatile imidazo[1,2‐a]pyridine structural motif, the substituents present in the obtained compounds allow specific synthetic elaboration to e. g. polycyclic fluorescent heterocycles.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11567/1020117
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