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 : 15 | Download : 9

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :Reaction of pyrimidine-insert ignore into journalissuearticles values(1H,3H,5H);-2,4,6-trione insert ignore into journalissuearticles values(barbituric acid);, 1,3-dimethyl pyrimidine-insert ignore into journalissuearticles values(1H,3H,5H);-2,4,6-trione insert ignore into journalissuearticles values(1,3-dimethyl barbituric acid);, and 1,3-diethyl-2-thioxodihydropyrimidine-4,6insert ignore into journalissuearticles values(1H,5H);- dione insert ignore into journalissuearticles values(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`insert ignore into journalissuearticles values(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 insert ignore into journalissuearticles values(thio);barbituric acids resulted in only monofunctionalized spiro[furo[2,3-d]pyrimidine-6,5`- pyrimidine]2,2`,4,4`,6`insert ignore into journalissuearticles values(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