Communications

Assembly of aldehydes and dimethylbarbituric acid into spirotricyclic furopyrimidines under the action of N-bromosuccinimide in water

M. N. Elinson, Yu. E. Ryzhkova, V. M. Kalashnikova, M. P. Egorov

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation

Abstract: A new type of chemical one-pot tandem Knoevenagel–Michael reaction followed by the NBS-induced cyclization was discovered. The reaction of aromatic aldehydes with two molecules of N,N'-dimethylbarbituric acid in the presence of NBS in water at ambient temperature affords spirotricyclic furopyrimidine scaffold, namely, 1,5-dihydro-2H,2'H-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]-2,2',4,4',6'-(1'H,3H,3'H)-pentones, in 90–98% yields.

Keywords: cascade reactions, tandem Knoevenagel–Michael reaction, benzaldehydes, barbituric acids, N-bromosuccinimide, oxidative cyclization, spirotricyclic compounds, furo[2,3-d]pyrimidines.

Received: 09.06.2025
Accepted: 16.06.2025

Language: English

DOI: 10.71267/mencom.7844

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