Catalyst-Free One-Pot Synthesis of Chromeno-Imidazo-Pyridinones by an Aza-Michael Addition/Rearrangement/Heterocyclization Tandem Reaction


A one-pot synthesis of a novel series of chromeno-imidazo-pyridinone derivatives from 3-[(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl]chromones and ethane-1,2-diamine at room temperature under catalyst-free conditions has been successfully developed. This approach involves a tandem aza-Michael addition reaction, a chromone-to-chromanone rearrangement, and a heterocyclization sequence, leading to chromeno-imidazo-pyridinone polyheterocycles. The structure and absolute configurations of the new compounds were elucidated by a combination of 1D- and 2D-NMR analyses and single-crystal X-ray diffraction.



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Lakhdari, H; Talhi, O; Hassaine, R; Taibi, N; Mendes, RF; Paz, FAA; Bennamane, N; Nedjar-Kolli, B; Bachari, K; Silva, AMS

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Thanks are due to University of Aveiro and FCT/MEC for the financial support of the QOPNA research project (FCT UID/QUI/00062/2013); to the CICECO-Aveiro Institute of Materials (POCI-01-0145-FEDER-007679; FCT UID/CTM/50011/2013), financed by national funds and, when appropriate, co-financed by FEDER under the PT2020 Partnership Agreement; and to the Portuguese NMR Network. We would like also to thank FCT/MEC and the General Directorate for Scientific Research and Technological Development-DGRSDT of Algeria and Agence Thematique de Recherche en Sciences et Technologie ATRST for approving the co-financed bilateral project PT-DZ/0005. We further wish to thank CICECO for funding the purchase of the singlecrystal X-ray diffractometer.

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