Synthesis of 1-tetralones by intramolecular Friedel-Crafts reaction of 4-arylbutyric acids using Lewis acid catalysts

Tetrahedron Letters

Volumn 44, Issue 21, 2003, Pages 4007-4010

  Cui, Dong Mei ^a   Kawamura, Masato ^a   Shimada, Shigeru ^a   Hayashi, Teruyuki ^a   Tanaka, Masato ^a,b  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Bismuth; Cyclization; Friedel Crafts reaction; Lewis acid; Tetralone

Indexed keywords

1 TETRALONE DERIVATIVE; 3 PHENOXYPROPIONIC ACID; 3 PHENYLTHIOPROPIONIC ACID; 4 CHROMANONE DERIVATIVE; BISMUTH DERIVATIVE; BUTYRIC ACID DERIVATIVE; GALLIUM; INDIUM; LANTHANIDE; LEWIS ACID; PROPIONIC ACID DERIVATIVE; THIOCHROMAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; FRIEDEL CRAFTS REACTION; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0038327870     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00855-4     Document Type: Article

References (27)

1. For example, see: (a) Deshpande, M. N.; Cain, M. H.; Patel, S. R.; Singam, P. R.; Brown, D.; Gupta, A.; Barkalow, J.; Callen, G.; Patel, K.; Koops, R.; Chorghade, M.; Foote, H.; Pariza, R. Org. Process Res. Dev. 1998, 2, 351-356; (b) Vukics, K.; Fodor, T.; Fischer, J.; Fellegvári, I.; Lévai, S. Org. Process Res. Dev. 2002, 6, 82-85.
2. For example, see: (a) Deshpande, M. N.; Cain, M. H.; Patel, S. R.; Singam, P. R.; Brown, D.; Gupta, A.; Barkalow, J.; Callen, G.; Patel, K.; Koops, R.; Chorghade, M.; Foote, H.; Pariza, R. Org. Process Res. Dev. 1998, 2, 351-356; (b) Vukics, K.; Fodor, T.; Fischer, J.; Fellegvári, I.; Lévai, S. Org. Process Res. Dev. 2002, 6, 82-85.
3. For example, see; (a) Wu, T. S.; Tsai, Y. L.; Damu, A. G.; Kuo, P. C.; Wu, P. L. J. Nat. Prod. 2002, 65, 1522-1525; (b) Quang, D. N.; Hashimoto, T.; Tanaka, M.; Baumgartner, M.; Stadler, M.; Asakawa, Y. J. Nat. Prod. 2002, 65, 1869-1874.
4. For example, see; (a) Wu, T. S.; Tsai, Y. L.; Damu, A. G.; Kuo, P. C.; Wu, P. L. J. Nat. Prod. 2002, 65, 1522-1525; (b) Quang, D. N.; Hashimoto, T.; Tanaka, M.; Baumgartner, M.; Stadler, M.; Asakawa, Y. J. Nat. Prod. 2002, 65, 1869-1874.
5. Martin E.L., Fieser L.F. Org. Synth. Coll. Vol. II. 1943;569-571.
6. Johnson G.D. Org. Synth. Coll. Vol. IV. 1963;900-903.
7. Krollpfeiffer F., Schäfer W. Ber. Dtsch. Chem. Ges. 56:1923;620-632.
8. Caro Y., Masaguer C.F., Ravina E. Tetrahedron: Asymmetry. 14:2003;381-387.
9. Snyder H.R., Werber F.X. Org. Synth. Coll. Vol. III. 1955;798-800.
10. Owton W.M., Brunavs M. Synth. Commun. 21:1991;981-987.
11. Rao A.V.R., Chanda B., Borate H.B. Tetrahedron. 38:1982;3555-3561.
12. Esteban G., Lopez-Sanchez M.A., Martinez E., Plumet J. Tetrahedron. 54:1998;197-212.
13. Premasagar V., Palaniswamy V.A., Eisenbraun E.J. J. Org. Chem. 46:1981;2974-2976.
14. Fieser L.F., Hershberg E.B. J. Am. Chem. Soc. 61:1939;1272-1281.
15. Yamato T., Hideshima C., Prakash G.K.S., Olah G.A. J. Org. Chem. 56:1991;3955-3957.
16. Olah G.A., Mathew T., Farnia M., Prakash G.K.S. Synlett. 1999;1067-1068.
17. Kooti M., Zendehdel M., Amini M.M. J. Inclusion Phenom. Macrocyclic Chem. 42:2002;265-268.
18. Desmurs J.R., Labrouillere M., Le Roux C., Gaspard H., Laporterie A., Dubac J. Tetrahedron Lett. 38:1997;8871-8874.
19. Repichet S., Le Roux C., Dubac J., Desmurs J.R. Eur. J. Org. Chem. 1998;2743-2746.
20. Le Roux C., Dubac J. Synlett. 2002;181-200.
21. Picot A., Repicheta S., Le Roux C., Dubac J., Roques N. J. Fluorine Chem. 116:2002;129-134.
22. Kawada A., Mitamura S., Matsuo J., Tsuchiya T., Kobayashi S. Bull. Chem. Soc. Jpn. 73:2000;2325-2333.
23. Matsuo J., Odashima K., Kobayashi S. Synlett. 2000;403-405.
24. Kobayashi S., Sugiura M., Kitagawa H., Lam W.W.L. Chem. Rev. 102:2002;2227-2302.
25. Prakash G.K.S., Yan P., Torok B., Bucsi I., Tanaka M., Olah G.A. Catal. Lett. 85:2003;1-6.
26. 4, filtered and concentrated under vacuum. The residue was separated by column chromatography on silica gel (hexane/EtOAc=10/1) to give 2a (32 mg, 88% yield).
27. 3O: C, 61.68; H, 4.24. Found: C, 61.87; H, 4.00.