A convenient synthesis of linear pyridinoimidazo[1,2-a]pyridine and pyrroloimidazo[1,2-a]pyridine cores |
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Authors: | Mounir Andaloussi Emmanuel Moreau Olivier Chavignon Jean C. Teulade |
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Affiliation: | Univ Clermont 1, UFR Pharmacie, Laboratoire de Chimie Organique, Clermont-Ferrand F-63001, France |
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Abstract: | Two new imidazo[1,2-a]pyridine derivatives, pyridinoimidazo[1,2-a]pyridine (10) and pyrroloimidazo[1,2-a]pyridine (16), were synthesised from 2-amino-4-methyl-5-nitropyridine (1) by linear cyclisation, making use of dimethylformamide dimethylacetal (DMFDMA) as an agent of vinylamine functionalisation. This report describes first the formation of pyridine and pyrroloimidazopyridine from (1), and then the formation of pyridine-fused and pyrrolo-fused pyridine by the Friedländer method and reductive cyclisation followed by treatment of the resulting adduct with chloroacetaldehyde. |
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Keywords: | Friedlä nder reaction Reductive cyclisation DMFDMA Pyridinoimidazo[1,2-a]pyridine Pyrroloimidazo[1,2-a]pyridine |
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