A novel one-pot synthesis of 3-carbomethoxy-4-arylfuran-2-(5H)-ones from ketones using [hydroxy(tosyloxy)iodo]benzene

Advances in Synthetic Applications of Hypervalent Iodine Compounds

“…Synthetic applications of this α-carbon functionalization include several one-pot reactions, such as α-alkoxylation or α-acetoxylation, α-iodination, α-azidation, and heterocyclization . In particular, the tosyloxylation of ketones followed by heterocyclization has been used in the syntheses of numerous heterocyclic systems, such as 2-aroylbenzo­[ b ]­furans, 3-aryl-5,6-dihydroimidazo­[2,1- b ]­[1,3]­thiazoles, 6-arylimidazo­[2,1- b ]­thiazoles, (1 S ,2 R )-indene oxide, 2-mercaptothiazoles, triazolo-[3,4- b ]-1,3,4-thiadiazines, dihydroindeno­[1,2- e ]­[1,2,4]­triazolo­[3,4- b ]­[1,3,4]­thiadiazines, furo­[3,2- c ]­coumarins, , 4,5-diarylisoxazoles, 2-substituted 4,5-diphenyloxazoles, quinoxaline, 3-carbomethoxy-4-arylfuran-2-(5 H )-ones, thiazol-2­(3 H )-imine-linked glycoconjugates, and other important heterocycles.…”

Convenient synthesis of symmetrical diketosulfides from enolizable ketones using [hydroxy(tosyloxy)iodo]benzene and na2S ⋅ 9H2O

“…The α-tosyloxy ketone, which is obtained easily from enolizable ketone by the reaction with HTIB is, therefore, considered as environmentally benign alternative to the toxic and lachrymatory α-haloketones. In continuation of our interest in hypervalent iodine reagents [8], herein we report the novel synthesis of diketosulfide by the reaction of enolizable ketones with HTIB, followed by treatment with Na 2 S · 9H 2 O (Scheme 2).…”

Hydroxy(tosyloxy)iodobenzene (HTIB): A Convenient Oxidizing Agent for the Synthesis of Heterocycles

“…This conversion is proceeded through the generation of α‐tosyloxyketones 4 by HTIB mediated oxidation of enolizable ketones 3 accompanied by the addition of potassium monomethyl malonate that results methyl 2‐oxo‐2‐arylethyl malonate 5 , which subsequently undergoes cyclization to the product 6 in good yields (63–76 %) (Scheme 2). [42] …”