General synthesis of 8-aryl-2-tetralones.
Two alternative routes are described for the synthesis of 8-aryl-2-tetralones (1). Route A starts from alpha-tetralone 3 and involves 3 or 4 steps, with the selective Na-EtOH reduction of 1-aryl-7-methoxynaphthalenes 2 being the key step. The exclusive reduction of the A ring of naphthalenes 2 occurs when the aryl group at C-1 has no substituent at the ortho positions, affording tetrahydronaphthalenes 11. Reduction of the B ring of 2 becomes the major process when the aryl fragment has two substituents at the ortho positions, affording 8-aryl-2-tetralones 1 as the major component. Route B involves 5 steps starting from 2-tetralone 5, with the key step being the Suzuki coupling with triflate 4. This approach allows the synthesis of 8-aryl-2-tetralones 1 with no substituent at the ortho positions of the aryl fragment and with naphthalene and anthracene rings at C-8.
Carreño
M Carmen
MC
Departamento de Química Orgánica (C-I), Universidad Autónoma, Cantoblanco, 28049 Madrid, Spain. carmen.carrenno@uam.es
Gonzalez-López
Marcos
M
Latorre
Alfonso
A
Urbano
Antonio
A
D015394:Molecular Structure; D013237:Stereoisomerism; D044024:Tetralones / Q000138:chemical synthesis* / Q000737:chemistry
D044024:Tetralones