- Turkish Journal of Chemistry
- Vol: 36 Issue: 6
- Bifunctionalized linked bis-spiro[furo[2,3-d]pyrimidine6,5 -pyrimidine]2,2 ,4,4 ,6 (3H ,3 H ,5H)-pen...
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
Authors : Nader Noroozi Pesyan, Mohammad Jalilzadeh
Pages : 788-804
Doi:10.3906/tar-1211-9
View : 9 | Download : 4
Publication Date : 9999-12-31
Article Type : Makaleler
Abstract :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.Keywords : Barbituric acid, bis-spiro[furo[2, 3-d]pyrimidine-6, 5'-pyrimidine], diastereomer, rotamer, cyanogen bromide