Flavonoids. 43 [1,2]. deprotonation-initiated aryl migration with sulfur dioxide extrusion: A route to 2,3-dihydro-2,3-diaryl-3-hydroxy-4h-1-benzopyran- 4-ones

T. Patonay, László Hegedüs, Erzsébet Patonay-Péli

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Treatment of trans-2,3-dihydro-2-aryl-3-nosyloxy-4H-1-benzopyran-4-ones with various bases afforded 2,3-dihydro-r-2-aryl-t-3-hydroxy-c-3-(4-nitrophenyl) -4H-1-benzopyran-4-ones in a deprotonation-initiated aryl migration followed by sulfur dioxide extrusion. In the presence of hydroxide and methoxide ions a secondary ring cleavage has also been observed. However, the reaction of trans-2,3-dihydro-2-aryl-3-nosyloxy-4H-1-benzopyran-4-ones with cyanide ions gave 2,3-dihydro-r-2-aryl-t-4-cyano-c-3,c-4-epoxy-4H-1-benzopyrans in a carbonyl attack of cyanide followed by an internal substitution reaction.

Original languageEnglish
Pages (from-to)145-151
Number of pages7
JournalJournal of Heterocyclic Chemistry
Volume30
Issue number1
DOIs
Publication statusPublished - 1993

Fingerprint

Sulfur Dioxide
Deprotonation
Flavonoids
Extrusion
Cyanides
Ions
Benzopyrans
Substitution reactions
benzopyran-4-one

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Flavonoids. 43 [1,2]. deprotonation-initiated aryl migration with sulfur dioxide extrusion : A route to 2,3-dihydro-2,3-diaryl-3-hydroxy-4h-1-benzopyran- 4-ones. / Patonay, T.; Hegedüs, László; Patonay-Péli, Erzsébet.

In: Journal of Heterocyclic Chemistry, Vol. 30, No. 1, 1993, p. 145-151.

Research output: Contribution to journalArticle

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