1,2-Aryl Shift in the Hypervalent Iodine Oxidation of Flavanones: A New Useful Synthesis of Isoflavones

Microwave-induced, solvent-free transformations of benzoheteracyclanones by HTIB (Koser`s reagent)

“…In boiling acetonitrile or propionitrile, isoflavone (4c) was the major product accompanied with a small amount of flavone (3c) and methyl 2-phenyl-2,3-dihydrobenzofuran-3-carboxylate. 13 The change of the solvent to methanol resulted in a dramatic shift as flavone (3c) became the major product, accompanied by some cis-3-methoxyflavanone and methyl 2-phenyl-2,3-dihydrobenzofuran-3-carboxylate. 14 The oxidative rearrangement of flavanone (1c)…”

Synthesis of new cis- and trans-3-hydroxy-2-(1-phenyl-3-aryl-4-pyrazolyl) chromanones using a hypervalent iodine oxidation approach

“…find interesting applications in flavonoids. [7][8][9][10][11][12][13][14] Among the various such applications, one remarkable use of IBD-KOH/MeOH system [15][16][17] is the availability of cis-3-hydroxyflavanones dimethylacetals, which can be converted into the corresponding trans-3-hydroxyflavanones and cis-3-hydroxyflavanones depending upon the hydrolytic conditions. cis-3-Hydroxyflavanones cannot be synthesized via conventional methods and pyrazole analogues of cis-and trans-3-hydroxycharmanones of the type 3 and 4 are unknown in literature.…”

A Novel Synthesis of New 3-Aryl-7-methylpyrano[4,3-b]pyran-4H,5H-diones Using Hypervalent Iodine(III) Reagents

“…In principle, two synthetic strategies based on the oxidative rearrangement of flavanones 8 5 and o-hydroxychalcones 9 7 to isoflavones 6 could be used for the present purpose. The first one (Equation 1) involves the application of [hydroxy(tosyloxy)iodo]benzene (HTIB), whereas the second one (Equation 2) makes the use of Tl(III) acetate.…”