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DOI: 10.1055/s-2002-35617
Synthesis of Isoflavones from 2′-Hydroxychalcones Using Poly[4-(diacetoxy)iodo]styrene or Related Hypervalent Iodine Reagent
Publikationsverlauf
Publikationsdatum:
20. November 2002 (online)
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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 the reaction mixture, no liberation of PhI, and reuse of the reagent.
Key words
chalcones - isoflavones - protecting groups - hypervalent iodine - oxidative rearrangements
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References
The amount of NaOH was calculated as follows: The amount (1.5 equiv) needed for the ring closure of acetal 2h-Bz plus the amount (3.0 equiv) of HOAc formed by decomposition of DIB and that of TsOH (2.0 equiv).
11Yields of one-pot synthesis of 3 from the corresponding 1-Bz using DIB/TsOH in CH2Cl2-MeOH are as follows: Isoflavones 3i (70%), 3j (77%), 3k (70%), and 3l (67%). In addition, the one-pot reactions of 1k-Bz with DIB/TsOH and PSDIB/TsOH proceeded without difficulty even in a mmol scale (a few grams), indicating the applicability of the present method for synthesis of a larger quantity as well. [16]
16The experiments were done as a part of our ongoing synthetic studies on isoflavonoids. Details will be submitted elsewhere.