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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 9
BKCSDE 32(9)
September 20, 2011 

New Strategy for the Synthesis of 5-Aryl-1H,1'H-spiro[furo[2,3-d]pyrimidine-6,5'- pyrimidine]2,2',4,4',6'(3H,3'H,5H)-pentaones and Their Sulfur Analogues
Mohammad Jalilzadeh, Nader Noroozi Pesyan *
Barbituric acid, Spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]pentaone, Cyanogen bromide, Uracil, L-(+)-Tartaric acid
Reaction of barbituric acid (BA), 1,3-dimethyl barbituric acid (DMBA) and 2-thiobarbituric acid (TBA) with cyanogen bromide and aldehydes in the presence of L-(+)-tartaric acid afforded a new route for the synthesis of stable heterocyclic 5-aryl-1H,1'H-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]2,2',4,4',6'(3H,3'H,5H)- pentaones which is a dimeric form of barbiturate (uracil and thiouracil derivative). In the reaction of 1,3-diethyl thiobarbituric acid (DETBA) the Knoevenagel condensation and then Michael adducts were obtained under the same condition. Structure elucidation is carried out by 1H NMR, 13C NMR, FT-IR and Mass analyses. Mechanism of the formation is discussed.
3382 - 3388
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