An able adjustment has been developed for regioselective aegis of 4-iodoimidazole application N,N-dimethylsulfamoyl chloride and 50% aqueous NaOH in THF arch to N,N-dimethylsulfamoyl-4-iodoimidazole in 97% crop and >98% purity. The barter of by-product 5-iodosulfonamide to the adapted artefact is a key affection of this procedure. (author abst.)Imidazole rings are begin in numberous accustomed compounds such as enzymes, nucleic acid, and alkaloids that play a role in biological processes.It is white solid.Melting point is 137-138°C.
The Stille coupling acknowledgment of stannylindole 12 with 4-iodoimidazole 13 (or 24) in the attendance of PdCl(2)(PPh) gave the agnate indole-imidazole coupling artefact 14 (or 25), thereby affording a new constructed access to the alkaloid granulatimide , abandoned from the Brazilian ascidian Didemnum granulatum, as able-bodied as its structural analogues, 10-methylgranulatimide , 17-methylgranulatimide , 10,17-dimethylgranulatimide .The Stille coupling acknowledgment of stannylindole 12 with 4-iodoimidazole 13 (or 24) in the attendance of PdCl2(PPh3)2 gave the agnate indole-imidazole coupling artefact 14 (or 25), thereby affording a new constructed access to the alkaloid granulatimide , abandoned from the Brazilian ascidian Didemnum granulatum, as able-bodied as its structural analogues, 10-methylgranulatimide , 17-methylgranulatimide , 10,17-dimethylgran-ulatimide.Despite all-encompassing analysis with altitude and attention groups, mixtures of the α- and β–isomers (∼3:2) were consistently obtained, and abominably the regioselectivity of the hydrostannylation acknowledgment could not be improved. The regiochemistry and the stereochemistry of this acknowledgment were bent by the magnitudes of the abreast coupling constants and Sn/H coupling constants. The imidazole-substituted propargyl booze 19 in about-face was able via a Sonogashira acknowledgment amid 4-iodoimidazole 18 and TBS-protected propargyl alcohol.
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