Bifunctionalized linked bis-spiro[furo[2,3-d]pyrimidine-6,5'- pyrimidine]2,2',4,4',6'(3H,3'H,5H)-pentaones derived from one-pot reaction of (thio)barbituric acids with aromatic dialdehydes and BrCN in the presence of Et3N

Reaction of pyrimidine-(1H,3H,5H)-2,4,6-trione (barbituric acid), 1,3-dimethyl pyrimidine-(1H,3H,5H)-2,4,6-trione (1,3-dimethyl barbituric acid), and 1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)- dione (1,3-diethyl thiobarbituric acid) with cyanogen bromide and aromatic dialdehydes in the presence of triethylamine leads to the selective and efficient formation of a novel class of bifunctionalized stable heterocyclic bis-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine] 2,2',4,4',6'(3H,3'H,5H)pentaones and their sulfur analogues, which are dimeric forms of barbiturate linked by a phenyl ring. A proposed mechanism was suggested for the formation of the products. The reaction of phthalaldehyde with BrCN and (thio)barbituric acids resulted in only monofunctionalized spiro[furo[2,3-d]pyrimidine-6,5'- pyrimidine]2,2',4,4',6'(3H,3'H,5H)pentaones, while isophthalaldehyde and terphthalaldehyde resulted in the bifunctionalized form.

Bifunctionalized linked bis-spiro[furo[2,3-d]pyrimidine6,5 -pyrimidine]2,2 ,4,4 ,6 (3H ,3 H ,5H)-pentaones derived from one-pot reaction of (thio)barbituric acids with aromatic dialdehydes and BrCN in the presence of Et3N

Reaction of pyrimidine-(1H,3H,5H)-2,4,6-trione (barbituric acid), 1,3-dimethyl pyrimidine-(1H,3H,5H)-2,4,6-trione (1,3-dimethyl barbituric acid), and 1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)- dione (1,3-diethyl thiobarbituric acid) with cyanogen bromide and aromatic dialdehydes in the presence of triethylamine leads to the selective and efficient formation of a novel class of bifunctionalized stable heterocyclic bis-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine] 2,2',4,4',6'(3H,3'H,5H)pentaones and their sulfur analogues, which are dimeric forms of barbiturate linked by a phenyl ring. A proposed mechanism was suggested for the formation of the products. The reaction of phthalaldehyde with BrCN and (thio)barbituric acids resulted in only monofunctionalized spiro[furo[2,3-d]pyrimidine-6,5'- pyrimidine]2,2',4,4',6'(3H,3'H,5H)pentaones, while isophthalaldehyde and terphthalaldehyde resulted in the bifunctionalized form.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

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A novel soluble phthalocyanine capable of binding four boronic esters

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Synthesis of 3-pyrroline-2-ones from amino acids and an aryl amine

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MWCNT/nano-ZrO2 as a new solid phase extractor: its synthesis, characterization, and application to atomic absorption spectrometric determination of lead

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Properties of the mixed adsorption layer: neutral detergent-tetramethylthiourea at interface electrode/solution

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Synthetic access to benzazolyl (pyrazoles, thiazoles, or triazoles)

Bakr Fathy ABDEL-WAHAB, Hanan Ahmed MOHAMED

Preparation of 2-(N,N-dialkylamino)-2,4,6- cycloheptatrien-1-one derivatives from an isocyanide, a primary amine, propionaldehyde, and tropolone via Ugi-Smiles coupling reaction in the presence of silica nanoparticles

Abdolhossain MASSOUDI, Issa AMINI, Ali RAMAZANI

Synthesis, structural characterization, and benzyl alcohol oxidation activity of mononuclear manganese(II) complex with 2,2'-bipyridine: [Mn(bipy)2(ClO4)2]

İbrahim KANİ, Mehmet KURTÇA

Efficient one-pot alkylation of imines using nanosilver iodide in aqueous media

Javad SAFAEI-GHOMI, Ahmad KAKAVAND-QALENOEI