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, Csaba Nemes, Tibor Timár, Gábor Tóth, Waldemar Adam

Research output: Contribution to journalArticle

26 Citations (Scopus)

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. Extension of this two-step procedure to 1-(2-hydroxyphenyl)-2-alken-1-ones was also accomplished. A strong preference for α cyclization was observed in the case of β-unsubstituted or -monoalkylated α,β-enones, while both 2,2-dimethyl-3-hydroxychromanones and 2-(1-hydroxy-1-methylethyl)-3-coumaranones were obtained from the β,β-dimethylated substrates.

Original languageEnglish
Pages (from-to)5375-5383
Number of pages9
JournalJournal of Organic Chemistry
Volume61
Issue number16
DOIs
Publication statusPublished - Aug 9 1996

Fingerprint

Flavanones
Cyclization
Epoxy Compounds
Epoxidation
Derivatives
Acids
Substrates
2'-hydroxychalcone
3-hydroxyflavanone
3-coumaranone

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and cyclization of 1-(2-hydroxyphenyl)-2-propen-1-one epoxides : 3-Hydroxychromanones and -flavanones versus 2-(1-hydroxyalkyl)-3-coumaranones. / Patonay, T.; Lévai, A.; Nemes, Csaba; Timár, Tibor; Tóth, Gábor; Adam, Waldemar.

In: Journal of Organic Chemistry, Vol. 61, No. 16, 09.08.1996, p. 5375-5383.

Research output: Contribution to journalArticle

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