title: A versatile and one-pot strategy to synthesize α-amino ketones from benzylic secondary alcohols using N-bromosuccinimide.
abstract: A metal-free one-pot strategy has been developed for the first time to synthesize pharmaceutically important α-amino ketones from readily available benzylic secondary alcohols and amines using N-bromosuccinimide. This new reaction proceeds via three consecutive steps involving oxidation of alcohols, α-bromination of ketones, and nucleophilic substitution of α-bromo ketones to give α-amino ketones. Importantly, this novel one-pot greener reaction avoids direct usage of toxic and corrosive bromine. This methodology has been employed efficiently to synthesize pharmaceutically important amfepramone and pyrovalerone in a single step.
authors: Department of Chemistry, Indian Institute of Technology Madras , Chennai, Tamil Nadu 600036, India.
authors: Somraj
authors: S
authors: Guha
authors: Venkatachalam
authors: V
authors: Rajeshkumar
authors: Surya Srinivas
authors: SS
authors: Kotha
authors: Govindasamy
authors: G
authors: Sekar
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D001974:Bromosuccinimide / Q000737:chemistry*; D002384:Catalysis; D004053:Diethylpropion / Q000138:chemical synthesis / Q000737:chemistry; D054879:Halogenation; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000588:Amines; D007659:Ketones; D011759:Pyrrolidines; D001974:Bromosuccinimide; D004053:Diethylpropion; C005719:pyrovalerone