title: Metal-Free Oxidative Nitration of α-Carbon of Carbonyls Leads to One-Pot Synthesis of Thiohydroximic Acids from Acetophenones.
abstract: A metal-free nitration of the α-C-H to carbonyl in propiophenones was achieved with I2/NaNO2 in the presence of an oxidant in dimethyl sulfoxide (DMSO) as the medium. Conversely under similar conditions, reaction of acetophenones produced thiohydroximic acids via a radical-based cascade event which involves oxidative nitration of the α-carbon to a carbonyl followed by Michael addition of the thiomethyl group from DMSO and subsequent rearrangement. Besides DMSO, the scope of the reaction encompasses other symmetrical and unsymmetrical dialkylsulfoxides.
authors.affiliation: Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute , Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India.
authors.forename: Shashikant U
authors.initials: SU
authors.lastname: Dighe
authors.affiliation: Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute , Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India.
authors.forename: Sushobhan
authors.initials: S
authors.lastname: Mukhopadhyay
authors.affiliation: Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute , Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India.
authors.forename: Kumari
authors.initials: K
authors.lastname: Priyanka
authors.affiliation: Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute , Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India.|Academy of Scientific and Innovative Research, New Delhi 110025, India.
authors.forename: Sanjay
authors.initials: S
authors.lastname: Batra