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

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

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

Russian journal of organic chemistry, 10/2020, Volume: 56, Issue: 10

Journal Article

A modified version of the three-component Biginelli reaction of 4-hydroxy-6-methyl-2 H -pyran-2-one with aromatic aldehydes and 1 H -benzimidazol-2-amine has been studied under thermal and microwave activation. Depending on the substituent in the initial aldehyde, angularly fused 5,6-dihydro-4 H -benzo4,5imidazo1,2- a pyranopyrimidin-4-ones or 2-amino-1 H -benzimidazol-3-ium arylbis(4-hydroxy-6-methyl-2-oxo-2 H -pyran-3-yl)methanides have been obtained. A plausible mechanism of their formation has been proposed.

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

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