title: Selective and multiple functionalization of pyridines and alkaloids via Mg- and Zn-organometallic intermediates.
abstract: Quinine, nicotine, and related electron-rich amino-substituted pyridines were readily metalated using LiCl-solubilized TMP (2,2,6,6-tetramethylpiperidyl) bases in the presence of BF(3)·OEt(2). A full pyridine functionalization of all five positions of the pyridine ring can be realized by using an appropriate combination of TMP bases in the presence or absence of BF(3)·OEt(2).
authors.affiliation: Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377 München, Germany.
authors.forename: Milica
authors.initials: M
authors.lastname: Jaric
authors.forename: Benjamin A
authors.initials: BA
authors.lastname: Haag
authors.forename: Sophia M
authors.initials: SM
authors.lastname: Manolikakes
authors.forename: Paul
authors.initials: P
authors.lastname: Knochel
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D009942:Organometallic Compounds; D011725:Pyridines; D008274:Magnesium; D015032:Zinc