Synthesis of methoxy and hydroxy containing tetralones: Versatile intermediates for the preparation of biologically relevant molecules

Tetrahedron Letters

Volumn 44, Issue 21, 2003, Pages 4145-4148

  Ghatak, Anjan ^a   Dorsey, James M ^a   Garner, Charles M ^a   Pinney, Kevin G ^a  

^a BAYLOR UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 HYDROXY 6 METHOXY 1 TETRALONE; CARBENE; HYDROXYL GROUP; KETONE DERIVATIVE; METHYL GROUP; TETRALONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ISOMER; OXIDATION; OXYGENATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038327776     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00715-9     Document Type: Article

References (16)

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10. Structure of tetralone ( 6 ) was confirmed by single-crystal X-ray analysis, Kautz, J.; Pinney, K. G. Baylor University, unpublished results, 2002.
11. 3) δ 2.11 (m, 2H), 2.60 (t, 2H, J=6.2 Hz), 2.93 (t, 2H, J=6.1 Hz), 3.95 (s, 3H), 5.75 (bs, 1H), 6.83 (d, 1H, J=8.6 Hz), 7.68 (d, 1H, J=8.6 Hz).
12. A thorough search of the peer-reviewed literature reveals no reference to tetralone 1a to date. However, after our study was complete, we discovered a report of the synthesis of this compound contained in two patent applications. This route relies on the initial synthesis of 5,6-dimethoxy-1-tetralone by a somewhat lengthy but noteworthy synthesis (Lahiri, S.; Ramarao, C.; Rao, B. V.; Rao, A. V. R.; Chorghade, M. S. Organic Process Research & Development, 1999, 3, 71) followed by the regioselective deprotection of the 5-methoxy group ((a) Denny, W. A.; Hutchings, R. H.; Johnson, D. S.; Kaltenbronn, J. S.; Lee, H. H.; Leonard, D. M.; Milbank, J. B. J.; Repine, J. T.; Rewcastle, G. W.; White, A. D. PCT Int. Appl., 2001, WO 01/79180; (b) Day, W. W.; Johnson, K. A.; Prakash, C. A.; Eggler, J. F. PCT Int. Appl., 2001, WO 01/77093). It is our contention that the route we describe in this manuscript is both highly versatile and extremely efficient in terms of preparing hydroxy and alkoxy containing tetralone analogs, and as such, is advantageous over the previously reported route.
13. 3) δ 2.08-2.14 (m, 2H), 2.32 (s, 3H), 2.36 (s, 3H), 2.61 (t, 2H, J=6.6 Hz), 2.74 (t, 2H, J=6.0 Hz), 7.69 (s, 1H).
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