Naphthyl cyanoketene < em > N < /em > , < em > S < /em > -acetals in glycoside synthesis: a new preparative route to a new class of < em > N < /em > -naphthylcyanoacrylamide thioglycosides and their conversions to naphthyl-pyrazole hybrids

Nucleosides Nucleotides Nucleic Acids. 2024 Jan 24:1-11. doi: 10.1080/15257770.2024.2305247. Online ahead of print.ABSTRACTThe novel N-naphthylcyanoacrylamide thioglycosides 4 were readily prepared by the reaction of N-napthylcyanoacetamide 1 with aryl isothiocyanates in the presence of potassium hydroxide, followed by coupling of the produced salts 2 with 2,3,4,6-tetra-O-acetyl-α-d-gluco- and galacto-pyranosyl bromides 3. The N-naphthyl acrylamide thioglycoside 12 was prepared by the reaction of N-napthylcyanoacetamide 1 with glucose isothiocyante 10 in the presence of potassium hydroxide, followed by alkylation of the produced salt 11 with methyl iodide. The reaction of thioglycoside compounds 4 with hydrazines afforded the corresponding naphthyl-pyrazole hybrids.PMID:38265284 | DOI:10.1080/15257770.2024.2305247
Source: Nucleosides, Nucleotides and Nucleic Acids - Category: Biochemistry Authors: Source Type: research