Abstract
Interaction of visnaginone or khellinone (1a,b) with cyanoacetamide, ethyl cyanoacetate or molanonitrile and elemental sulfur in presence of triethylamine afforded thiophene enamino derivatives (2a-d) respectively according to Gewald method. Acetylation of 2a with acetic anhydride gave 3. Condensation of 2b with p-chlorobenzaldehyde yielded 4. Compound 6 was afforded from reaction of enamino carboxamide (2b) with thiourea.. Compound 2b reacted with benzoyl chloride to give thienopyrimidine (8). N-phenyl thienopyrimidine (11) and N-amino thienopyrimidine (13) were prepared from reaction of 2c with phenyl isothiocyanate and hydrazinolysis of 12 with hydrazine hydrate.
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