title: N-Bromosuccinimide promoted and base switchable one pot synthesis of α-imido and α-amino ketones from styrenes.
abstract: An N-Bromosuccinimide (NBS) promoted one pot strategy for the synthesis of α-amino functionalized aryl ketones starting from commercially available styrenes has been developed. NBS participates in multiple tasks, such as bromonium ion formation, oxidation of bromohydrin and providing a nucleophilic nitrogen source. The reaction can easily be switched between α-imido and α-amino ketones by the choice of base. This one pot strategy was successfully applied for the synthesis of psychoactive drug candidates, amfepramone, mephedrone and 4-MEC.
authors.affiliation: Department of Chemistry, Savitribai Phule Pune University (Formerly: University of Pune), Ganeshkhind Road, Pune-411007, Maharashtra, India. uakshirsagar@chem.unipune.ac.in uakshirsagar@gmail.com.
authors.forename: Mahesh H
authors.initials: MH
authors.lastname: Shinde
authors.forename: Umesh A
authors.initials: UA
authors.lastname: Kshirsagar
mesh_terms: D000588:Amines / Q000737:chemistry*; D001974:Bromosuccinimide / Q000737:chemistry*; D007094:Imides / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013343:Styrenes / Q000737:chemistry*
chemical_list: D000588:Amines; D007094:Imides; D007659:Ketones; D013343:Styrenes; D001974:Bromosuccinimide