title: 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.
abstract: 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.
authors.affiliation: Albany Molecular Research, Inc., 21 Corporate Circle, Albany, New York 12212-5098, USA.
authors.forename: Peter R
authors.initials: PR
authors.lastname: Guzzo
authors.forename: Ronald N
authors.initials: RN
authors.lastname: Buckle
authors.forename: Ming
authors.initials: M
authors.lastname: Chou
authors.forename: Sean R
authors.initials: SR
authors.lastname: Dinn
authors.forename: Michael E
authors.initials: ME
authors.lastname: Flaugh
authors.forename: Anton D
authors.initials: AD
authors.lastname: Kiefer
authors.forename: Kendal T
authors.initials: KT
authors.lastname: Ryter
authors.forename: Anthony J
authors.initials: AJ
authors.lastname: Sampognaro
authors.forename: Steven W
authors.initials: SW
authors.lastname: Tregay
authors.forename: Yao-Chang
authors.initials: YC
authors.lastname: Xu
mesh_terms: 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
chemical_list: D002227:Carbazoles; D005464:Fluorobenzenes; D005663:Furans; D006845:Hydrocarbons, Fluorinated; C109453:LY 344864; D010091:Oximes; D012701:Serotonin