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http://nopr.niscpr.res.in/handle/123456789/9236| 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] |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| IJCB 44B(12) 2575-2581.pdf | 136.13 kB | Adobe PDF | View/Open |
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