Reactions of some 1,3-diaminonucleophiles with azlactones
Abstract
Triethylamine-mediated reactions ofS-substituted isothiouronium halides (2) with unsaturated aziactones (1) gave the corresponding S-substituted 2-thiopyrimidines (3), S-substituted 3-thioacrylanilide (10), and 4-benzylidene-2-iminoimidazolidin-5-one (13), depending on the ethoxy, anilino, and phenyl substituents, respectively, at the 4-C![[double bond, length half m-dash]](https://www.rsc.org/images/entities/char_e006.gif)
C bond. Aminolyses of (3) afforded 2-aminopyrimidines (4). Tautomerism of compounds (3) and (13) was confirmed by their acetylation and/or hydrolysis. Basemediated condensation of compound (1c) with thiourea or urea in boiling ethanol was unsuccessful, but simple heating of these reactants at an elevated temperature gave 4-benzylidene-2-phenylimidazol-5(4H)-one (22).
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