Studies on 2,4-Dithioxo and 2-Thioxoimidazolidene Derivatives

Abstract

5,5-Dimethylimidazolidine-2,4-dithione ( 1 ) undergoes a Mannich reaction to give 5,5-dimethyl-3-(4-morpholinomethyl)imidazolidine-2,4-dithione ( 2 ), which on treatment with (2,3,4,6-tetra-O-acetyl-α -D-glucopyranosyl)bromide (ABG) afforded 5,5-dimethyl-3(4-morpholinomethyl)-2-(2′,3′,4′,6′-tetra-O-acetyl-β -D-thioglucopyranosyl)-4-thiohydantoin ( 3 ). Oxidation of 3 with KMnO₄ furnished the corresponding sulfone 4 . Deblocking of 3 with sodium ethoxide afforded 1 . Reaction of 1 with ABG gave the N-glucoside 5 . Deblocking of 5 afforded 5,5-dimethyl-3-N-(3,4,5-trihydroxy-6-hydroxy-methyltetrahydropyran-2-yl)imidazolidine-2,4-dithione ( 6 ). Oxidation of 5 yielded 5,5-dimethyl-imidazolidine-3-N-(2′,3′,4′,6′-tetra-O-acetyl-β -D-glucopyranosyl)-2-oxo,4-thione ( 7 ). Reaction of 1 with phenacyl chloride afforded 8 , which on thiation with P₄S₁₀ gave 9 . 5-Benzylidene-2-thioxoimidazolidin-4-one ( 10 ) reacted with some halo compounds and afforded 11 and 12 . Treatment of 10 with 2,4-dinitro-1-chlorobenzene afforded N,N-dimethyl-2,4-dinitrobenzamide ( 13 ) and 2-benzylidene-6-nitro-2H-benzo[d]imidazo[2,1-b]thiazol-3-one ( 14 ). Refluxing 12 with semicarbazides gave 15 and 16 . Boiling 12 with 4-aminoacetophenone furnished 18 , which on treatment with hydrazine gave 5-benzylidene-2-[4-(1-hydrazonoethyl)phenylimino]imidazolidin-4-one ( 19 ). Conden-sation of 18 with benzaldehyde yielded 5-benzylidene-2-[4-(3-phenylacryoyl)phenylimino]-imidazolidin-4-one ( 20 ).

Keywords:

• Alkylation
• glucoside
• hydrazide
• HIV
• microbial activity
• imidazolidines
• mannich bases

Acknowledgments

The authors are thankful to the Danish International Development Agency (DANIDA) for their support. Thanks are also due to Dr. Ahmed I. Mowaad, Biochemistry Department, Faculty of Agriculture, El-Fayoum University, El-Fayoum, Egypt, for testing antimicrobial activity.