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Biginelli Synthesis of Regioisomeric 5,6-Dihydro-4H-benzo[4,5]imidazo[1,2-a]pyranopyrimidin-4-ones

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Abstract

A modified version of the three-component Biginelli reaction of 4-hydroxy-6-methyl-2H-pyran-2-one with aromatic aldehydes and 1H-benzimidazol-2-amine has been studied under thermal and microwave activation. Depending on the substituent in the initial aldehyde, angularly fused 5,6-dihydro-4H-benzo[4,5]imidazo[1,2-a]pyranopyrimidin-4-ones or 2-amino-1H-benzimidazol-3-ium arylbis(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)methanides have been obtained. A plausible mechanism of their formation has been proposed.

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Funding

This study was performed under financial support by the Russian Foundation for Basic Research (project no. 20-03-00446).

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Authors and Affiliations

  1. Institute of Chemistry, Chernyshevsky Saratov National Research State University, 410012, Saratov, Russia

    I. V. Kanevskaya, A. S. Bondartsova & O. V. Fedotova

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  1. I. V. Kanevskaya
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  2. A. S. Bondartsova
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  3. O. V. Fedotova
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Correspondence to I. V. Kanevskaya.

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Kanevskaya, I.V., Bondartsova, A.S. & Fedotova, O.V. Biginelli Synthesis of Regioisomeric 5,6-Dihydro-4H-benzo[4,5]imidazo[1,2-a]pyranopyrimidin-4-ones. Russ J Org Chem 56, 1753–1757 (2020). https://doi.org/10.1134/S1070428020100139

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