title: One-pot synthesis of 2-aminoquinoline-based alkaloids from acetonitrile.
abstract: α-Diaminoboryl carbanions, readily prepared from acetonitrile, stereoselectively convert 2-nitrobenzaldehydes into nitrophenyl (Z)-acrylonitriles. Subsequent reductive cyclization leads to a series of 2-aminoquinoline derivatives. The entire procedure is practically operated in a single flask.
authors.affiliation: Department of Chemistry and Biochemistry, University of Mississippi, University, MS 38677, USA. tomioka@olemiss.edu
authors.forename: Takashi
authors.initials: T
authors.lastname: Tomioka
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Takahashi
authors.forename: Toshihide
authors.initials: T
authors.lastname: Maejima
mesh_terms: D000097:Acetonitriles / Q000138:chemical synthesis / Q000737:chemistry*; D000181:Acrylonitrile / Q000138:chemical synthesis / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000634:Aminoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods; D003500:Cyclization; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000097:Acetonitriles; D000470:Alkaloids; D000634:Aminoquinolines; D000181:Acrylonitrile; C032159:acetonitrile