A highly effective one-pot synthesis of quinolines from o-nitroarylcarbaldehydes.
A highly effective one-pot Friedländer quinoline synthesis using inexpensive reagents has been developed. o-Nitroarylcarbaldehydes were reduced to o-aminoarylcarbaldehydes with iron in the presence of catalytic HCl (aq.) and subsequently condensed in situ with aldehydes or ketones to form mono- or di-substituted quinolines in high yields (66-100%).
Li
An-Hu
AH
Department of Cancer Chemistry, OSI Pharmaceuticals, Inc., 1 Bioscience Park Drive, Farmingdale, NY 11735, USA. ali@osip.com
Ahmed
Eilaf
E
Chen
Xin
X
Cox
Matthew
M
Crew
Andrew P
AP
Dong
Han-Qing
HQ
Jin
Meizhong
M
Ma
Lifu
L
Panicker
Bijoy
B
Siu
Kam W
KW
Steinig
Arno G
AG
Stolz
Kathryn M
KM
Tavares
Paula A R
PA
Volk
Brian
B
Weng
Qinghua
Q
Werner
Doug
D
Mulvihill
Mark J
MJ
D000447:Aldehydes / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry*; D007501:Iron / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D001547:Benzaldehydes; D007659:Ketones; D011804:Quinolines; C043850:2-nitrobenzaldehyde; D007501:Iron