A Convenient Synthesis of 7-Halo-1-indanones and 8-Halo-1-tetralones

Journal of Organic Chemistry

Volumn 68, Issue 26, 2003, Pages 10195-10198

  Nguyen, Phong ^a   Corpuz, Evelyn ^a   Heidelbaugh, Todd M ^a   Chow, Ken ^a   Garst, Michael E ^a  

^a ALLERGAN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC HYDROLYSIS; AMINO KETONES;

ACIDITY; HYDROLYSIS; OXIDATION; POTASSIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

KETONES;

3 CHLORO 1 (2 HALOPHENYL)PROPAN 1 ONE; 7 AMINOINDAN 1 ONE; 7 HALO 1 INDANONE; 8 AMINOTETRAL 1 ONE; 8 HALO 1 TETRALONE; ACETAMIDE DERIVATIVE; ACETONE; INDANONE DERIVATIVE; KETONE DERIVATIVE; N (5,6,7,8 TETRAHYDRONAPHTHALEN 1 YL)ACETAMIDE; N INDAN 4 YL ACETAMIDE; PERMANGANATE POTASSIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; FRIEDEL CRAFTS REACTION; HYDROLYSIS; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

HYDROCARBONS, HALOGENATED; INDANS; TETRALONES;

EID: 0346362496     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035289s     Document Type: Article

References (31)

1. Tagat, J. R.; McCombie, S. W.; Nazareno, D. V.; Boyle, C. D.; Kozlowski, J. A.; Chackalamannil, S.; Josien, H.; Wang, Y.; Zhou, G. J. Org. Chem. 2002, 67, 1171.
2. (a) Deady, L. W.; Desneves, J.; Kaye, A. J.; Thompson, M.; Finlay, G. J. ; Baguley, B. C.; Denny, W. A. Bioorg. Med. Chem. 1999, 7, 2801.
3. (b) Thorsett, E. D.; Stermitz, F. R. Synth. Commun. 1972, 2, 375.
4. Feiser, L. F.; Berliner, E. J. Am. Chem. Soc. 1952, 74, 536.
5. (a) GB 1249375, 1971.
6. (b) Babin, D.; Demoute, J.-P. WO 8908096, 1989.
7. (a) Godel, T.; Gutknecht, E.-M. EP 0 606 661 B1, 1994.
8. (b) Sneikus, V. Chem. Rev. 1990, 90, 879.
9. (c) Panetta, C. A.; Dixit, A. S. Synthesis 1981, 59.
10. Kenner, J.; Witham, E. J. Chem. Soc. 1921, 119, 1452.
11. Biggs, D. F.; Casy, A. F.; Chu, I.; Coutts, R. T. J. Med. Chem. 1976, 4, 472.
12. Morita, S.; Otsubo, K.; Matsubara, J.; Ohtani, T.; Uchida, M. Tetrahedron: Asymmetry 1995, 6, 245.
13. (a) Sugimori, M.; Ejima, A.; Ohsuki, S.; Uoto, K.; Mitsui, I.; Matsumoto, K.; Kawato, Y.; Yasuoka, M.; Sato, K.; Tagawa, H.; Terasawa, H. J. Med. Chem. 1994, 37, 3033.
14. (b) Sugimori, M.; Ejima, A.; Ohsuki, S.; Uoto, K.; Mitsui, I.; Kawato, Y.; Hirota, Y.; Sato, K.; Terasawa, H. J. Med. Chem. 1998, 2, 375.
15. (c) Olson, R. E.; Maduskuie, T. P.; Thompson, L. A.; Tebben, A. J.; Wang, N.; Deng, W.; Liu, H. WO 01/60826 A2.
16. Shaabani, A.; Bazgir, A.; Teimouri, F.; Lee, D. G. Tetrahedron Lett. 2002, 43, 5165.
17. Hahn, R. C.; Howard, P. H.; Lorenzo, G. A. J. Am. Chem. Soc. 1971, 93, 5816.
18. Doyle, M. P.; Siegfried, B.; Dellaria, J. F. J. Org. Chem. 1977, 42, 2426.
19. (a) Blum, J.; Bergmann, E. D. J. Org. Chem. 1967, 32, 342.
20. (b) Doyle, M. P.; Bryker, W. J. J. Org. Chem. 1979, 44, 1572.
21. Sircar, I.; Duell, B. L.; Cain, M. H.; Burke, S. E.; Bristol, J. A. J. Med. Chem. 1986, 29, 2142.
22. (a) Layer, R. W.; MacGregor, I. R. J. Org. Chem. 1956, 21, 1120.
23. (b) Matsumoto, T.; Hata, K. J. Am. Chem. Soc. 1957, 79, 5506.
24. (c) Bartmann, W.; Konz, E.; Ruger, W. J. Heterocycl. Chem. 1987, 24, 677.
25. (a) Roe, A. Org. React. 1949, 5, 193.
26. (b) Zenitz, B. L.; Hartung, W. H. J. Org. Chem. 1946, 11, 444.
27. (c) Suschitzky, H. Adv. Fluorine Chem. 1965, 4, 1.
28. (d) Yakobson, G. G.; D'yachenko, A. I.; Bel'chikova, F. A. Zh. Obshch. Khim. 1962, 32, 849 (translated).
29. (a) Hino, T.; Uehara, H.; Takashima, M.; Kawate, T.; Seki, H.; Hara, R.; Kuramochi, T.; Nakagawa, M. Chem. Pharm. Bull. 1990, 38, 2632.
30. (b) Atwal, K. S.; Ferrare, F. N.; Ding, C. Z.; Grover, G. J.; Sleph, P. G.; Dzwonczyk, S.; Baird, A. J.; Normandin, D. E. J. Med. Chem. 1996, 39, 304.
31. (c) Sandmeyer reaction: Tietze, L. F.; Nordmann, G. Eur. J. Org. Chem. 2001, 3247.