Synthesis of Aurones by the Oxidative Rearrangement of 2′-Hydroxychalcones with Thallium (III) Nitrate

Synthesis of isoflavones

“…Although the thallium(III) nitrate oxidation of the 2'hydroxychalcones usually provides isoflavones 6, in some special cases a mixture of isoflavones 6 and aurones 17 or aurone 17 as sole isolable product are obtained. First example for the aurone formation by the oxidation of 2'hydroxychalcones 1 6 with thallium(III) nitrate was described by Lévai and Tó´kés in 1982 [157]. A mechanism has also been suggested for this transformation (Scheme 12).…”

Synthesis of Isoflavones

“…First example for the aurone formation by the oxidation of 2'hydroxychalcones 1 6 with thallium(III) nitrate was described by Lévai and Tó´kés in 1982 [157]. First example for the aurone formation by the oxidation of 2'hydroxychalcones 1 6 with thallium(III) nitrate was described by Lévai and Tó´kés in 1982 [157].…”

Oxidative cyclization in the synthesis of 5‐ and 6‐membered N,O‐heterocycles

“…Thallium(III) nitrate (TTN) has been used to effect oxidative cyclization of various phenolic substrates via rearrangement [68]. It has been found that the reaction course is sensitive to the nature of substituents [69,70].…”