Unexpected products in the multicomponent reaction of sodium azide,barbituric acid, and arylglyoxal

The derivatives of barbituric acid, commonly known as barbiturates, have a special place in pharmaceutical chemistry because of their biological activities such as hypnotic, sedative, anticonvulsant, antimicrobial, anaesthetic, anticancer and antitumor properties [1,2]. Substances of the barbituricacid group have been used thera-peutically for many years. Due to the chemical structure of barbituricacid and its capabilityto make keto–enol form, it has a unique potential to beusedas a valuable building block in various organic reactions. Here we wish to report the result of our study on the reaction of arylglyoxals 1, barbituric acid 2 and sodium azide 3 in green solvent lead to products 4. The structures of this products were proved by 1H-NMR, 13C-NMR and IR spectral data and elemental analysiss. To a mixture of â-dicarbonyl compound (1 mmol) in ethanol (5 mL), were added arylglyoxal (1 mmol), sodium azide (1 mmol) And room thempreture for 30 min . After removing the solvent under reduced pressure, the crude productwas purified by washing with diethyl ether. 5-(1-ammonio-2-argio-1-(1,3- dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl)-2-oxoethyl)-1,3-dimethyl-2,4,6- trioxohexahydropyrimidin-5-ide.Yellow powder Yield: 98%. IR (KBr) (ῡmax, cm-1):; 3372 (NH3), 1670 (C=O). 1H- NMR (400 MHz DMSO-d6): δ 2.42 (12H,s, CH3), 6.02 (1H, s, CH), 7.42 (2H, d, 3JHH= 8 Hz, HAr), 7.71 (2H, d , 3JHH= 8Hz, HAr ), 10.1 (3H, s, NH3 ).