Reactions of 4-(4-Methylbenzoyl)-5-(4-Methylphenyl)-2,3- Furandione With Semi-/Thiosemi-Carbazones

Abstract

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.

Synthesis and Characterization of Diazenyl-1,3-diphenylpropane-1,3-dione and 5-[Hydroxy(phenyl)methyl]-4-phenylpyrimidine Derivatives

“…Acetophenone semicarbazone and acetophenone thiosemicarbazone reacted with furan-2,3-diones and 1-methylenaminopyrimidine derivatives were synthesized. The N-aminopyrimidine derivatives (1a-f) were used as important materials in the synthesis of the target heterocycles (Scheme-I) [6][7][8][9][10][11] . Briefly, the reactions of 1a-f were carried with 1,3-diketones and NaBH 4 .…”

“…Some of them are frequently encountered in many drugs used for the treatment of hypothyroidy, hypertension, cancer chemotherapy and HIV infection [1][2][3][4][5] . There are published reports about the synthesis of some pyrimidine derivatives from furan-2,3diones [6][7][8][9][10][11] (Scheme-I). Also conformational analysis and quantum chemical calculations were carried out by means of MMP2, CNDO, MNDO and AM1 approximation methods for a series of compounds which are functionalized pyrimidine derivatives 8,9 .…”

Pre-versus postoperative tramadol instillation: both are effective for decreasing pain and/or agitation in pediatric adenotonsillectomy

“…Synthesis 1-Aminopyrimidine-2(1H)-thione (LH, 1) was prepared according to the literature method by a 2-step synthesis process. 26,27 The ligand and its complexes were very stable at room temperature in the solid state. The ligand is soluble in common organic solvents, but its metal complexes are generally only soluble in DMF and DMSO.…”

Crystal structure of 3-[4-(pyrimidin-2-yl)piperazin-1-ium-1-yl]butanoate

“…For general background and pharmacological properties of fused heterocyclic derivatives, see: Amin et al (2009); Ibrahim & El-Metwally (2010); Kuyper et al (1996); Onal & Yıldırım (2007); Padmaja et al (2009); Tollefson et al (1991). For pharmacological properties of pyrimidines, see: Burdge (2000).…”

“…Pyrimidines in general have been of much interest for biological and medical reasons and thus their chemistry has been investigated extensively (Onal & Yıldırım, 2007) and in many drugs used for the treatment of hypothyroidism and hypertension, in cancer chemotherapy or HIV infections (Burdge, 2000) and with related fused heterocyclic compounds that exhibit biological activities such as anticancer (Amin et al, 2009), antiviral (Ibrahim & El-Metwally, 2010), antibacterial (Kuyper et al, 1996 and antioxidant (Padmaja et al, 2009). Some pyrimidinylpiperazinyl compounds like buspirone and BuSpar (Tollefson et al, 1991) are used to treat anxiety.…”