An imidazo[1,5-a]pyridine derivative was unexpectedly obtained through the action of Fe2+ on a dynamic library of imines generated in situ via condensation of benzaldehyde and 2-picolylamine. The reaction product was easily isolated as the only nitrogen-containing product eluted from the chromatographic column. A reaction mechanism is proposed, in which combined kinetic and thermodynamic effects exerted by Fe2+ on the various steps of the complex reaction sequence are discussed. The Fe2+ nature of the added metal cation was found to be pivotal for the achievement of the imidazo[1,5-a]pyridine derivative as well as its amount in the reaction mixture. When the electronic effects were evaluated, gratifying yields were obtained only in the presence of moderately electron-releasing or moderately electron-withdrawing groups on the aldehyde reactant. No traces of imidazo[1,5-a]pyridine derivatives were obtained for p-OCH3 and p-NO2 benzaldehyde.

Formation of Imidazo[1,5-a]pyridine Derivatives Due to the Action of Fe2+ on Dynamic Libraries of Imines / Albano, Simone; Olivo, Giorgio; Mandolini, Luigi; Massera, Chiara; Ugozzoli, Franco; Di Stefano, Stefano. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 82:7(2017), pp. 3820-3825. [10.1021/acs.joc.7b00381]

Formation of Imidazo[1,5-a]pyridine Derivatives Due to the Action of Fe2+ on Dynamic Libraries of Imines

MASSERA, Chiara;UGOZZOLI, Franco;
2017

Abstract

An imidazo[1,5-a]pyridine derivative was unexpectedly obtained through the action of Fe2+ on a dynamic library of imines generated in situ via condensation of benzaldehyde and 2-picolylamine. The reaction product was easily isolated as the only nitrogen-containing product eluted from the chromatographic column. A reaction mechanism is proposed, in which combined kinetic and thermodynamic effects exerted by Fe2+ on the various steps of the complex reaction sequence are discussed. The Fe2+ nature of the added metal cation was found to be pivotal for the achievement of the imidazo[1,5-a]pyridine derivative as well as its amount in the reaction mixture. When the electronic effects were evaluated, gratifying yields were obtained only in the presence of moderately electron-releasing or moderately electron-withdrawing groups on the aldehyde reactant. No traces of imidazo[1,5-a]pyridine derivatives were obtained for p-OCH3 and p-NO2 benzaldehyde.
Formation of Imidazo[1,5-a]pyridine Derivatives Due to the Action of Fe2+ on Dynamic Libraries of Imines / Albano, Simone; Olivo, Giorgio; Mandolini, Luigi; Massera, Chiara; Ugozzoli, Franco; Di Stefano, Stefano. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 82:7(2017), pp. 3820-3825. [10.1021/acs.joc.7b00381]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2826430
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