| Abstract: | Functionalisation of Iodopyrazoles with D-Glucopyranose and with Aminoalcohols, Respectively . 3, 4, 5-Triiodo-pyrazole ( 1a ) and 3, 4-diiodo-5-methyl-1 H-pyrazole ( 1 b ) were silylated with hexamethyldisilazane without isolation of the N-trimethylsily derivatives and than glucosilated to give the β-N-nucleosides 2a and 2b , respectively, with 2, 3, 4, 6-tetra-O-acetyl-α-D-glucopy-ranosylbromide or -fluoride in the presence or absence of SnCl4. The corresponding deacetylated derivatives 3 a – b can be easily obtained by treatment of 2 a – b with sodium methanolate in methanol. Furthermore, 1 a and 1 b as well as 3(5)-methoxycarbonyl-4-iodo-1-H-pyrazole ( 1 c ) were alkylated with methyl bromoacetate-acetate to form the corresponding pyrazole-1-yl-methylacetates 4 a – c . These compounds could be amidated by short heating with N-methylglucamine and 1-amino-propane-2, 3-diol (isoserinol), respectively, in methanol to form the corresponding amides 5 a – c and 6 a – c . The diamide 7 c was prepared bylongtime heating of 4 c with excess isoserinol in n-propanol. |
