Behzat Altural

Reactions of cyclic oxalyl compounds, part 29: A simple synthesis of functionalized 1H-pyrimidines

Summary4-Benzoyl-5-phenylfuran-2,3-dione (1) and the semicarbazones2, ureas and thioureas6, respectively, combine with loss of water and carbondioxide yielding the 1H-pyrimidine derivatives3 and7, respectively, in moderate yields (30–75%). Hydrolysis of3 b leads to the 1-amino-pyrimidine-2-one4.Zusammenfassung4-Benzoyl-5-phenylfuran-2,3-dion (1) cyclisiert mit den Semicarbazonen2 sowie den Harnstoffen bzw. Thioharnstoffen6 unter Verlust von H2O und CO2 zu einer Reihe von 1,4,5-substituierten 1H-Pyrimidinen in Ausbeuten von 30–75%. Die an3 b exemplarisch durchgeführte Hydrolyse liefert die 1-Amino-Verbindung4.

Reactions of cyclic oxalyl compounds, Part 30: Some reactions with N-amino-pyrimidine derivatives

Summary1-Amino-5-benzoyl-4-phenyl-1H-pyrimidine derivatives1 add arylisocyanates2 to give the N,N′-disubsituted ureas3 which can be cyclized by use of oxalyl dichloride to the imidazolyl-pyrimidinones(thiones)4. In addition,1 is transferred into the desaminated pyrimidines6 either by diazotation reaction or by thermolysis of the parental functionalized pyrimidine derivatives7.Zusammenfassung1-Amino-5-benzoyl-4-phenyl-1H-pyrimidin-2-one(thione)1 addieren Arylisocyanate2 in guten Ausbeuten (60–95%) zu den Pyrimidinylharnstoff-Derivaten3, die ihrerseits mit Oxalylchlorid zu den Imidazolyl-pyrimidinen4 cyclisierbar sind. Versuche, die Amino-Verbindungen1 zu diazotieren, führen unter N2-Eliminierung zu den desaminierten Pyrimidinen6, die andererseits auch durch einfache Thermolyse der Methylenamino-pyrimidine7 entstehen.

3-Acetyl-4-benzoyl-2-methyl-5-phenyl-3,3a-di­hydro­pyrazolo­[2,3-c]pyrimidine-7(6H)-thione

The molecule of the title compound, C(22)H(19)N(3)O(2)S, is not planar. The dihedral angle between the two phenyl rings is 27.46 (7) degrees and in the dihydropyrazolopyrimidine ring the total puckering amplitude Q(T) is 0.526 (3) A. The structure is stabilized by both intra- and intermolecular C-H.O interaction, and by an intermolecular N-H.S hydrogen bond.