Silver(I) oxide-mediated facile and practical sulfonylation of alcohols

Synthesis and Biological Activities of New 1,2,4-Triazol-3-one Derivatives

“…Sulfonates, which have been used as important intermediates in organic synthesis and possess antiviral, anti-HIV or anticancer activity [15,16], are usually obtained by treatment of the corresponding alcohols with sulfonating agents in the presence of pyridine or triethylamine. Moreover, tetramethylalkylidenediamine and silver(I) oxide were reported to be efficient reagents for the sulfonylation of alcohols in the presence of sulfonyl chlorides; the latter reagent is being used in the presence of a catalytic amount of potassium iodide [17]. In addition, several sulfonylation reactions were achieved in aqueous sodium hydroxide when sufficiently hydrophilic alcohols were used [18,19].…”

Triazole-oligomers by 1,3-dipolar cycloaddition

“…The hexa-azide core 6 was prepared by the reaction of 4b and 3,5-bis(azidomethyl)phenol 7, which was synthesized in four steps from commercially available 5-hydroxyisophthalic acid (8). Thus, methyl ester derivative 9 was obtained quantitatively by refluxing 8 in methanol in the presence of a catalytic amount of H 2 SO 4 .…”

“…Reaction of oligoethylene glycol 14a with TsCl in the presence of Ag 2 O, KI and K 2 CO 3 gave the corresponding tosylate 15a in 55% yield which was converted to the di-azide 16a using NaN 3 in 91% yield. 8 Similarly, starting from the oligoethyleneoxide glycol 14b and 14c, we prepared the tosylate 15b and 15c in 93 and 96% yield respectively which on reaction with NaN 3 gave the corresponding oligoethyleneoxide diazide 16b and 16c in 80 and 85% yield (Scheme 4). 16a, n = 2; 91% 16b, n = 3; 80% 16c, n = 5; 85% 14a, n = 2 14b, n = 3 14c, n = 5 15a, n = 2; 55% 15b, n = 3; 93% 15c, n = 5; 96%…”

Syntheses of Precursors and Reference Compounds of the Melanin-Concentrating Hormone Receptor 1 (MCHR1) Tracers [11C]SNAP-7941 and [18F]FE@SNAP for Positron Emission Tomography

“…Compounds 35 and 36 were used for tosylation yielding 2-(tosyloxy)ethyl ester TOE@SNAP 3 and 3-(tosyloxy)propyl ester TOP@SNAP 5, respectively. Since common tosylation methods [30][31][32] were not applicable, tosylation was achieved using silver oxide and tosyl chloride in the presence of potassium iodide adapting a method of Bouzide et al [33]. Comparing the yields, TOE@SNAP 3 was obtained with 63%, whereas the tosylpropyl derivative 5 gave a poorer 31% yield (Scheme 12).…”

“…Product 31 was obtained as a yellow-brownish oil (133 mg, 49.4%). (33). Under an argon atmosphere a mixture of N-(3-(piperidin-4-yl)phenyl)acetamide (28) (239 mg, 1.09 mmol), 2-(t-butyldiphenylsilyloxy)ethyl 3-((3-bromopropyl)carbamoyl)-4-(3,4-difluorophenyl)-6(methoxymethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (26, 775 mg, 1.04 mmol) and K 2 CO 3 (1.52 g, 11.00 mmol) in ACN (40 mL) was stirred at 35 °C for 37 h. The resulting yellow suspension was filtered and the filtration residue was washed with EtOAc.…”