Preparation of 8-Amido-2-dimethylamino-1,2,3,4-tetrahydro-2-dibenzofurans and several fluorinated derivatives via [3,3]-sigmatropic rearrangement of O-aryloximes.
Methodology to prepare 8-amido-2-amino-1,2,3,4-tetrahydro-2-dibenzofurans, analogues with a fluorine substituent incorporated in the 6-, 7-, and 9-positions, and a difluorinated analogue with fluorines in the 6- and 9-positions is described. The tetrahydrodibenzofuran ring systems are prepared by acid-catalyzed [3,3]-sigmatropic rearrangement of O-aryloximes. Regioselective reactions to prepare the requisite O-aryloxime intermediates from commercially available fluorobenzene derivatives are discussed.
Guzzo
Peter R
PR
Albany Molecular Research, Inc., 21 Corporate Circle, Albany, New York 12212-5098, USA.
Buckle
Ronald N
RN
Chou
Ming
M
Dinn
Sean R
SR
Flaugh
Michael E
ME
Kiefer
Anton D
AD
Ryter
Kendal T
KT
Sampognaro
Anthony J
AJ
Tregay
Steven W
SW
Xu
Yao-Chang
YC
D002227:Carbazoles / Q000737:chemistry; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D020650:Combinatorial Chemistry Techniques; D005464:Fluorobenzenes / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry*; D012701:Serotonin / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D002227:Carbazoles; D005464:Fluorobenzenes; D005663:Furans; D006845:Hydrocarbons, Fluorinated; C109453:LY 344864; D010091:Oximes; D012701:Serotonin