Synthesis and Cyclization of 1-(2-Hydroxyphenyl)-2-propen-1-one Epoxides: 3-Hydroxychromanones and-flavanones versus 2-(1-Hydroxyalkyl)-3-coumaranones

T Patonay, A Lévai, C Nemes, T Timár…

Index: Patonay, Tamas; Levai, Albert; Nemes, Csaba; Timar, Tibor; Toth, Gabor; Adam, Waldemar Journal of Organic Chemistry, 1996 , vol. 61, # 16 p. 5375 - 5383

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Citation Number: 29

Abstract

Competitive α and β cyclization of 2'-hydroxychalcone epoxides affords 2-(α-hydroxybenzyl)- 3-coumaranone and/or 3-hydroxyflavanones, which depends on the conditions employed. Epoxidation of 2'-hydroxychalcones by dimethyldioxirane followed by either base-or acid- catalyzed ring closure provides a novel, general, and efficient method for the synthesis of trans-3-hydroxyflavanones, which includes also the naturally occurring derivatives. ...