FLAVONOIDS, 40. SYNTHESIS OF 3-ALKYL- AND -ARYLTHIOFLAVANONES AND THEIR TRANSFORMATIONS INTO SULFUR-CONTAINING FLAVONOIDS

Article abstract of DOI:10.1016/S0040-4020(01)81494-0

trans-3-Mesyloxyflavanones 1 were converted into cis- and trans-3-(alkylthio)- and -(phenylthio)flavanones 2-4 by nucleophilic substitution reaction with thiols or thiolates.Flavanones 2-4 were useful intermediates in the synthesis of various sulfur-containing derivatives; flavanones, flavones and dihydrochalcones posessing alkyl- or arylthio, -sulfinyl and -sulfonyl group.Oxidation of cis- and trans- isomers of 4 led to completely different products.