title: A general and efficient 2-amination of pyridines and quinolines.
abstract: Pyridine N-oxides were converted to 2-aminopyridines in a one-pot fashion using Ts2O-t-BuNH2 followed by in situ deprotection with TFA. The amination proceeded in high yields, excellent 2-/4-selectivity, and with good functional group compatibility. 2-Amino (iso)quinolines were also obtained in the same manner. Combined with the simple oxidation of pyridines to pyridine N-oxides, this method provides a general and efficient way for amination of 2-unsubstituted pyridines.
authors.affiliation: Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA. jingjun_yin@merck.com
authors.forename: Jingjun
authors.initials: J
authors.lastname: Yin
authors.forename: Bangping
authors.initials: B
authors.lastname: Xiang
authors.forename: Mark A
authors.initials: MA
authors.lastname: Huffman
authors.forename: Conrad E
authors.initials: CE
authors.lastname: Raab
authors.forename: Ian W
authors.initials: IW
authors.lastname: Davies
mesh_terms: D000586:Amination; D000631:Aminopyridines / Q000138:chemical synthesis*; D000634:Aminoquinolines / Q000138:chemical synthesis*; D011725:Pyridines / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry*
chemical_list: D000631:Aminopyridines; D000634:Aminoquinolines; D011725:Pyridines; D011804:Quinolines; C013229:pyridine N-oxide; C032439:alpha-aminopyridine