The 4-(4-methylbenzoyl)-5-(4-methylphenyl)-2,3-furandione (1) and various semi-/thiosemicarbazones 2a-h combine with loss of carbondioxide and water yielding l-methylenaminopyrimidine-2-one and -thione derivatives 3a-h, in moderate yields (43-59%). Hydrolysis of 5-(4-methylbenzoyl)-l-(methyl-4methylphenyimethylenamino)-4-(4-methylphenyl)-1 //-pyrimidine-2-one (3c) and 5-(4-methylbenzoyl)-4-(4methylphenyl)-l-(phenylmethylenamino)-l//-pyrimidine-2-thione (3h) lead to the l-amino-5-(4methylbenzoyl)-4-(4-methylphenyl)-l//-pyrimidine-2-one (4) and the l-amino-5-(4-methylbenzoyl)-4-(4-). The newly synthesized compounds were characterized by elemental analyses, IR, 'H and l3 C NMR spectral data. All were compared with their previous analogues. Brought to you by | Purdue University Libraries Authenticated Download Date | 5/27/15 6:26 AM Vol. 13, Nos. 2-3, 2007 Reactions of 4-(4-methylbenzoyl)-5-(4-methylphenyl)-2,3-Furandione with semi-thiosemi-carbazones much interest for biological and medical reasons, thus their chemistry have been investigated extensively 25 . In particulary, various analogues of pyrimidines possess effective herbicidal, antibacterial, antifungal, antiviral 26 ' 27 . Some of them are frequently encountered in many drugs used for the treatment of hypothyroidy, hypertension, cancer chemotherapy or HIV infection 28 31 . In the present study, we carried out the reactions of 1 with several semi-/thiosemi-carbazones 2a-h, obtained from semi-/thiosemi-carbazide and the corresponding carbonyl compounds in our laboratories, yielding the new series of l-methyleneaminopyrimidine-2-one and -thione derivatives 3a-h. The
l-Amino-5-(4-methylbenzoyl)-4-(4-methylphenyl)-l//-pyrimidine-2-thione (5).20 mL of water and 5 mL of acetic acid were added to a solution of 1 g 3h in 20 mL of butanol and the mixture was the heated under reflux for 45-50 minutes. With cooling 0.46g (58%) of 5 precipitated and was recrystallized from ethanol; m.p.