General synthesis of 8-aryl-2-tetralones.

Abstract

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.

Cite this paper

@article{Carreno2006GeneralSO, title={General synthesis of 8-aryl-2-tetralones.}, author={Mauro Carreno and Marcos Antonio Gonz{\'a}lez-L{\'o}pez and Alfonso Latorre and Antonio Urbano}, journal={The Journal of organic chemistry}, year={2006}, volume={71 13}, pages={4956-64} }