Heterocycles p. 1397 - 1414 (2016)
Update date:2022-08-17
Topics:
Abdel Reheim, Mohamed Ahmed Mahmoud
Abdel Hafiz, Ibrahim Saad
Elian, Mohamed Ahmed
The reaction of 6-phenyl-2-thioxo-2,3-dihydropyrimidin-4(5H)-one 1 with acetyl chloride in acetic anhydride in the presence of sodium acetate afforded 5-acetyl-6-phenyl-2-thioxo-2,3-dihydropyrimidin-4(5H)-one 2 which reacted with bromine, hydrazine hydrate, phenylhydrazine, cyanothioacetamide, aldehydes and (malononitrile/sulfur) to give 2-thioxo-2,3-dihydropyrimidine derivatives 4, 7a,b, 8, 10 and 11 respectively. In the present investigation 6-phenyl-2-thioxo-2,3-dihydropyrimidin-4(5H)-one 1 was reacted with chloroacetyl chloride to yield the corresponding compound 13. Compound 1 was reacted with some electrophilic reagents such as (benzylidene-cyanothioacetamide derivatives, 2-cyano-2-cyclopentylethanethioamide, 2-cyano-2-cyclohexylethanethioamide and aromatic diazonium salts) to give compounds 23, 27a,b and 35 respectively. The newly synthesized heterocycles were characterized on the basis of their chemical properties and spectral data.
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