Mechanism of cyclization of substituted 2′-hydroxychalcones to flavanones
- 1 January 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 5,p. 633-639
- https://doi.org/10.1039/p29850000633
Abstract
The conversion of 2′-hydroxy-(3), 2′,4′-dihydroxy-(4), 2′,3-dihydroxy-(5), and 2′,4-dihydroxy-chalcone (6) in aqueous alkali; and of (3) and 2′-hydroxy-4-nitrochalcone (7) in alkaline methanolic medium into the corresponding substituted flavanones has been studied kinetically and spectroscopically. It has been found that results from both methods are consistent with the existence of chalcones in the trans-s-cis conformation and indicate a mechanism that involves general acid attack to the ionized form of the 2′-hydroxychalcones, rotation through the CO–Cα bond and annelation to the flavanone.Keywords
This publication has 0 references indexed in Scilit: