US EPA

7626293 

Journal Article 

General synthesis of 8-aryl-2-tetralones 

Carreño, MC; Gonzalez-López, M; Latorre, A; Urbano, A; , 

2006 

Yes 

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 

AMER CHEMICAL SOC 

WASHINGTON 

71 

13 

4956-4964 

English 

16776527 

10.1021/jo060688j 

WOS:000238312300033 

https://pubs.acs.org/doi/10.1021/jo060688j
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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.