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http://dx.doi.org/10.5012/bkcs.2011.32.9.3382

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  

Jalilzadeh, Mohammad (Department of Chemistry, Faculty of Science, Urmia University)
Pesyan, Nader Noroozi (Department of Chemistry, Faculty of Science, Urmia University)
Publication Information
Bulletin of the Korean Chemical Society / v.32, no.9, 2011 , pp. 3382-3388 More about this Journal
Abstract
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, $^{13}C$ NMR, FT-IR and Mass analyses. Mechanism of the formation is discussed.
Keywords
Barbituric acid; Spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]pentaone; Cyanogen bromide; Uracil; L-(+)-Tartaric acid;
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