One pot InCl3-catalyzed synthesis of 1-glycosylmethyl-1H-imidazoles

Abstract

A series of 1-glycosylmethyl-4,5-diphenyl-1H-imidazoles with six different glycosyls were obtained in 48-55% yields from the multicomponent reaction of the corresponding C-glycosyl methylamines, formaldehyde, benzil, and ammonium acetate under catalysis with indium(III) chloride in methanol at ambient temperature. Starting with C--D-glucopyranosyl or C--Dgalactopyranosyl methylamines, the procedure also was examined with phenylglyoxal or glyoxal instead of benzil, and the pertinent 1--D-glycopyranosylmethyl-4-phenyl-1Himidazole and -5-phenyl-1H-imidazole or 1--D-glycopyranosylmethyl-1H-imidazole derivatives were prepared and isolated. Of four differently 4-and 5-substituted 1-(-Dglucopyranosylmethyl)-1H-imidazoles, only the 5-phenyl derivative exhibited a weak inhibition of rabbit muscle glycogen phosphorylase b (IC 50 = 125 μM).

Synthesis, Characterization, Antimicrobial Evaluation, and Computational Investigation of Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives

“…Therefore, studies on the synthesis, characterization, and biological activity of imidazole, 1,3,4-thiadiazole, and the derivatives of these compounds are being intensively pursued. [4][5][6][7] Thiadiazole is a heterocyclic aromatic compound with a fivemember ring with two nitrogen atoms and one sulfur atom. This compound has four different isomeric forms found in nature: 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, and 1,3,4-thiadiazole.…”

Design, Synthesis, SAR and Molecular Modeling Studies of Novel Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives as Highly Potent Antimicrobial Agents

“…Heterocyclic compounds are one of the most preferred compounds in antimicrobial studies and many involve the imidazole, 1,3,4‐thiadiazole and their derivatives. Hence, synthesis and characterization of such bioactive compounds containing imidazole and 1,3,4‐thiadiazole are being studied intensely . Furthermore, the synthesis of compounds including these bioactive groups with various biological activities is currently being studied .…”

Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

“…al. described [45] the synthesis of 1‐glycosylmethylated imidazoles 55 as a novel group of carbohydrate mimetics starting from C ‐glycosyl methylamines 53 with formaldehyde, ammonium acetate and 1,2‐dicarbonyl compounds 54 such as benzil, phenyl glyoxal and glyoxal in presence of InCl 3 as catalyst through one‐pot multicomponent reaction (scheme 14).…”