One-pot New Barbituric Acid Derivatives Derived from the Reaction of Barbituric Acids with BrCN and Ketones

Hosseini Y., Rastgar S., HEREN Z., Buyukgungor O., Pesyan N. N.

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, vol.58, no.3, pp.309-318, 2011 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 58 Issue: 3
  • Publication Date: 2011
  • Doi Number: 10.1002/jccs.201190031
  • Journal Name: JOURNAL OF THE CHINESE CHEMICAL SOCIETY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.309-318
  • Keywords: Barbituric acid, Teriethylammonium-5-bromo-2,4,6-trioxohexahydropyrimidin-5-ide, Uracil, CYANOGEN-BROMIDE REACTION, ELECTROCHEMICAL OXIDATION, ANALOGS, CONDENSATION, CYANATION, CHEMISTRY
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

Reaction of cyclic P-dicarbonyl compounds such as pyrimidine-(1H,3H,511)-2,4,6-trione (BA), 1,3-dimethyl pyrimidine-(1H,3H,5H)-2,4,6-trione (DMBA) and 2-thioxo-pyrimidine-(1H,3H,5H)-4,6-dione (TBA) with cyanogen bromide in acetone and 2-butanone in the presence of triethylamine afforded a new class of stable heterocyclic spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]2,2',4,4',6'(3H,3'H,5H)-pentaones (dimeric forms of barbiturate) at 0 degrees C and ambient temperature. Structure elucidation was carried out by X-ray crystallographic, H-1 NMR, C-13 NMR, two dimensional NMR, FT-IR spectra, mass spectrometry and elemental analysis. The mechanism of product formation is discussed. The reaction of DMBA with cyanogen bromide in the presence of triethylamine also afforded trimeric form of barbiturate of uracil derivatives in good yield. The reaction of selected acyclic beta-dicarbonyl compounds with cyanogen bromide in the presence of triethylamine in acetone and/or diethyl ether has also been investigated under the same condition. Diethyl malonate and ethyl cyanoacetate brominated and also ethyl acetocetate both brominated and cyanated on active methylene via cyanogen bromide.