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Title: Synthesis of isoflavones containing naturally occurring substitution pattern by oxidative rearrangement of respective flavanones using thallium(III) p-tosylate
Authors: Singh, Om V
Muthukrishnan, M
Sunderavadivelu, M
Keywords: Thallium(III) p-tosylate;oxidative rearrangement;isoflavones;flavanones;2,3-aryl migration
Issue Date: Dec-2005
Publisher: CSIR
IPC Code: Int.Cl.7 C 07 D
Abstract: Claisen condensation of substituted 2'-hydroxyacetophenones 1a-c with aromatic aldehydes affords respective substituted 2'-hydroxychalcones 2a-n which on base catalyzed cyclization in pyridine : methanol : water (1:1:1) give respective flavanones 3a-n. The oxidative rearrangement of flavanones with thallium (III) p-tosylate furnishes respective isoflavones 4a-n in overall 62-72% yields starting from 1. The present methodology has been successfully applied for the synthesis of naturally occurring isoflavones such as di-O-methyldaidzein 4a, cabruvin 4b, pseudobabtigenin methylether 4d, 5,7-dimethoxyisoflavone 4f, 5,7,4'-trimethoxyisoflavone 4g, derrustone 4i, 7,8,3',4'-tetramethoxyisoflavone 4l, purpuranin-A 4m and 7,8,3',4',5'-pentamethoxyisoflavone 4n and thus the first synthesis of 4n is reported.
Page(s): 2575-2581
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.44B(12) December 2005]

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