A facile preparation of tetralins from arene-1,4-diones using titanium(IV) chloride and triethylsilane

Tetrahedron Letters

Volumn 52, Issue 50, 2011, Pages 6827-6830

  Li, Gang ^a   Xiao, Qiong ^a   Li, Chun ^a   Wang, Xiaojian ^a   Yin, Dali ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Arene 1,4 dione; Intramolecular cyclization; Ionic hydrogenation; Tetralin

Indexed keywords

TETRALIN DERIVATIVE; TITANIUM DERIVATIVE;

ARTICLE; CATALYST; CYCLIZATION; HYDROGENATION; SYNTHESIS;

EID: 80755187911     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.10.054     Document Type: Article

References (13)

1. R. Perrone, F. Berardi, N.A. Colabufo, M. Leopoldo, V. Tortorella, F. Fiorentini, V. Olgiati, A. Ghiglieri, and S. Govoni J. Med. Chem. 38 1995 942
2. W.M. Welch, A.R. Kraska, R. Sarges, and B.K. Koe J. Med. Chem. 27 1984 1508
3. S.D. Wyrick, R.G. Booth, A.M. Myers, C.E. Owens, N.S. Kula, R.J. Baldessarini, A.T. McPhail, and R.B. Mailman J. Med. Chem. 36 1993 2542
4. B.B. Hook, L. Cortizo, and A.M. Johansson J. Med. Chem. 39 1996 4036
5. J.W. Cook, and C.L. Hewett J. Chem. Soc. 1933 1098
6. E. Bergmann Chem. Rev. 29 1941 529
7. N. Hiyoshi, R. Miura, C.V. Rode, O. Sato, and M. Shirai Chem. Lett. 34 2005 424
8. M.T. Bogert, D. Davidson, and P.M. Apfelbaum J. Chem. Soc. 56 1934 959
9. R.O. Roblin, D. Davidson, and M.T. Bogert J. Chem. Soc. 57 1935 151
10. P.J. Kropp, G.W. Breton, S.L. Craig, S.D. Crawford, W.F. Durland, J.E. Jones, and J.S. Raleigh J. Org. Chem. 60 1995 4146
11. S.W. Youn, S.J. Pastine, and D. Sames Org. Lett. 6 2004 581
12. K. Xie, S. Wang, P. Li, X. Li, Z. Yang, X. An, C.-C. Guo, and Z. Tan Tetrahedron Lett. 51 2010 4466
13. 4, and the solvent was removed. Flash chromatography of the residue over silica gel using petroleum ether as the eluent afforded the pure 1-methyl-tetralin (2a). The product was identified by NMR and MS and the data are identical to the reported values.