A general and efficient 2-amination of pyridines and quinolines.
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.
Yin
Jingjun
J
Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA. jingjun_yin@merck.com
Xiang
Bangping
B
Huffman
Mark A
MA
Raab
Conrad E
CE
Davies
Ian W
IW
D000586:Amination; D000631:Aminopyridines / Q000138:chemical synthesis*; D000634:Aminoquinolines / Q000138:chemical synthesis*; D011725:Pyridines / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry*
D000631:Aminopyridines; D000634:Aminoquinolines; D011725:Pyridines; D011804:Quinolines; C013229:pyridine N-oxide; C032439:alpha-aminopyridine