Synthesis of some new S-glycosyl pyrimidine and condensed pyrimidine derivatives

Abstract

Mercaptopyrimidine ( 4 ) was synthesized by the reaction of isothiocyanate and acrylate ( 1 ). It was allowed to react with preacetylated sugar bromide and/or halomethylene derivatives to produce alkylated pyrimidines ( 5 , 7a - d ). Hydrolysis of compound ( 5 ) produced compound ( 6 ). Interacyclization of compounds ( 7a - d ) afforded thienopyrimidines ( 8a - d ). Moreover oxidation of compound ( 7b ) gave the corresponding thienopyrimidine dioxide ( 9 ). Cyanoethylation of compound ( 4 ) afforded compound ( 10 ) that reacted with hydrazine hydrate to give pyrazolopyrimidine ( 11 ). Oxidation of compound 4 afforded bisulphide ( 12 ). The cycloaddition product ( 13 ) was obtained by reaction of compound 4 with maleic anhydride. Pyrimidopyrimidine, pyrimidopyridazine and tetrazolopyriminde derivatives ( 16 - 20 ) were obtained by reaction of 4-chloropyrimidine ( 15 ) with thiourea, benzilhydrazone and sodium azide, respectively. N- alkylated pyrazolopyrimidine ( 21 ) was obtained by reaction of compound ( 15 ) with acetophenonehydrazone.