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 ).
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.