title: New one-pot synthesis of spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]pentaones and their sulfur analogues.
abstract: Reaction of barbituric acid (BA), 1,3-dimethyl barbituric acid (DMBA) and 2-thiobarbituric acid (TBA) with cyanogen bromide and various aldehydes in presence of triethylamine afforded a new class of heterocyclic stable 5-alkyl and/or 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 are dimeric forms of barbiturate (uracil and thiouracil derivatives) at 0 °C to ambient temperatures. Structure elucidation is proved by X-ray crystallography, (1)H NMR, (13)C NMR, FT-IR, CHN and mass analyses techniques. Mechanisms of the formations are discussed.
authors.affiliation: Department of Chemistry, Faculty of Science, Urmia University, 57159 Urmia, Iran.
authors.forename: Mohammad
authors.initials: M
authors.lastname: Jalilzadeh
authors.forename: Nader
authors.initials: N
authors.lastname: Noroozi Pesyan
authors.forename: Fereshteh
authors.initials: F
authors.lastname: Rezaee
authors.forename: Saeed
authors.initials: S
authors.lastname: Rastgar
authors.forename: Yaser
authors.initials: Y
authors.lastname: Hosseini
authors.forename: Ertan
authors.initials: E
authors.lastname: Sahin
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001463:Barbiturates / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D018360:Crystallography, X-Ray; D003488:Cyanogen Bromide / Q000737:chemistry; D005021:Ethylamines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010422:Pentanones / Q000138:chemical synthesis* / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013858:Thiobarbiturates / Q000737:chemistry
chemical_list: D000447:Aldehydes; D001463:Barbiturates; D005021:Ethylamines; D010422:Pentanones; D011743:Pyrimidines; D013141:Spiro Compounds; D013858:Thiobarbiturates; C018924:1,3-dimethylbarbituric acid; C029684:thiobarbituric acid; D003488:Cyanogen Bromide; C016162:triethylamine; C032232:barbituric acid