Stereochemical studies of 2-hydroxychromanones by 1H NMR spectroscopy

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Abstract

2-Hydroxychromanones (2a-2f) were synthesized by ring closing of 2-hydroxyacetophenones (1a, b) and 2-hyroxypropiophenones (1c-1f). In the case of 2-hydroxy-3-methyl-chromanones (2c-2f) a mixture of cis and trans isomers was obtained. The trans isomers are conformalionally homogeneous, the cis isomers exist in a conformational equilibrium. At room temperature the isomers are transformed into each other via opening of the heteroring. This process becomes faster in alkaline medium and the β-diketo form 4 can also be observed.

Original languageEnglish
Pages (from-to)2307-2312
Number of pages6
JournalTetrahedron
Volume37
Issue number12
DOIs
Publication statusPublished - 1981

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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