[PDF][PDF] An improved and eco-friendly method for the synthesis of flavanone by the cyclization of 2'-hydroxy chalcone using methane sulphonic acid as catalyst

P Kulkarni, P Wagh, P Zubaidha�- Chemistry Journal, 2012 - researchgate.net
P Kulkarni, P Wagh, P Zubaidha
Chemistry Journal, 2012researchgate.net
Flavanones are important biosynthetic precursors for the synthesis of flavones, isoflavones,
flavonols and dihydroflavonols. The flavanone skeleton is present in a wide range of
synthetic and naturally occurring products exhibiting various interesting pharmacological
activities. The present paper describes the use of methane sulphonic acid as an efficient
organocatalyst for the synthesis of substituted flavanones from 2'-Hydroxy Chalcones in
good yields and in short reaction time. The catalytic efficiency of methane sulphonic acid in�…
Abstract
Flavanones are important biosynthetic precursors for the synthesis of flavones, isoflavones, flavonols and dihydroflavonols. The flavanone skeleton is present in a wide range of synthetic and naturally occurring products exhibiting various interesting pharmacological activities. The present paper describes the use of methane sulphonic acid as an efficient organocatalyst for the synthesis of substituted flavanones from 2’-Hydroxy Chalcones in good yields and in short reaction time. The catalytic efficiency of methane sulphonic acid in cyclization of chalcones to flavanones has been demonstrated with a variety of substrates bearing electron–deficient to electron rich groups on chalcones and the yields obtained are higher than the reported methods with triflluoroacetic acid/mineral acids. Methane sulphonic acid is an inexpensive, safe, eco-friendly acid catalyst with low LD50. The present protocol could find wide spread application in the synthesis of flavanones bearing free hydroxyl groups on the aromatic moiety. At the same time the methodology would be useful for the synthesis of naturally occurring bioactive flavanones.
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