Unusual sulfanylation through ring transformation of arene-tethered 2H-pyran-2-ones by in situ built Michael adduct

A novel synthesis of highly functionalized alkylsulfanylmethyl arenes 8a–m through the ring transformation of 6-aryl-4-methyl/ethylsulfanyl-2H-pyran-2-one-3-carbonitriles 1a–j, by reaction with methyl vinyl ketone 2, is delineated and illustrated. To ascertain the course of reaction, 3-arylsulfanylmethyl-2-methyl-6-methylsulfanyl-4-phenylbenzonitriles 8k–m were also prepared from the reaction of 1 with 4-arylsulfanyl-butan-2-ones 7c,d.