2002
DOI: 10.1055/s-2002-35617
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Synthesis of Isoflavones from 2′-Hydroxychalcones Using Poly[4-(diacetoxy)iodo]styrene or Related Hypervalent Iodine Reagent

Abstract: Isoflavones are synthesized in an one-pot reaction by treating the hypervalent iodine(III) reagent, [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser's reagent) with 2¢-benzoyloxychalcones in MeOH. A combined use of (diacetoxyiodo)benzene (DIB)/p-toluenesulfonic acid (TsOH) is also effective for the same purpose. As an extension of these monomeric reagents, polymer-supported DIB {PSDIB, poly[4-(diacetoxy)iodo]styrene} with TsOH works also well. The merits of the latter are the ease of separation of isoflavones from … Show more

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Cited by 49 publications
(14 citation statements)
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“…In the chalcone route, a chalcone substrate is generated by an aldol reaction between an appropriate acetophenone and an aromatic aldehyde. Oxidative rearrangement of the chalcone substrate by utilizing either a thallium(III) or hypervalent iodide reagent in methanol, followed by base-mediated ring closure, yields the final desired products [26]. Although these two routes are used to construct bulk quantities of synthetic genistein, other methods such as the Suzuki-Miyaura cross-coupling of arylboronic acids and halochromones are often used to generate smaller amounts of material for biological analysis [27, 28].…”
Section: Genistein: Structure and Epidemiologymentioning
confidence: 99%
“…In the chalcone route, a chalcone substrate is generated by an aldol reaction between an appropriate acetophenone and an aromatic aldehyde. Oxidative rearrangement of the chalcone substrate by utilizing either a thallium(III) or hypervalent iodide reagent in methanol, followed by base-mediated ring closure, yields the final desired products [26]. Although these two routes are used to construct bulk quantities of synthetic genistein, other methods such as the Suzuki-Miyaura cross-coupling of arylboronic acids and halochromones are often used to generate smaller amounts of material for biological analysis [27, 28].…”
Section: Genistein: Structure and Epidemiologymentioning
confidence: 99%
“…The synthesis of chromones starting from o-hydroxyketones or related compounds has also been reported through an intramolecular cyclization of aryl ethynylketones [154] or 2-acetoxy- [155], benzyloxy- [156], or hydroxychalcones [157], followed by oxidation.…”
Section: 44mentioning
confidence: 99%
“…[162] The reaction can also be performed using PIFA, [163] or PIDA in the presence of TsOH (Scheme 85). [164] This transformation has been employed as key step in the synthesis of isoflavone natural products.…”
Section: Aminohalogenationmentioning
confidence: 99%