394
A. K. Sharma et al. / Tetrahedron 63 (2007) 389–395
J. Med. Chem. 1976, 19, 472–475; (k) Rufer, C.; Kessler,
H.-J.; Schroder, E. J. Med. Chem. 1975, 18, 253–258.
2. For intramolecular Friedel–Crafts acylation reactions, see: (a)
Smith, M. B.; March, J. Advanced Organic Chemistry.
Reactions, Mechanisms, and Structure, 5th ed.; Wiley: New
York, NY, 2001; pp 712–714; (b) Heaney, H. Comprehensive
Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon:
Oxford, UK, 1991; Vol. 2, pp 753–768; (c) Sethna, S.
Friedel–Crafts and Related Reactions; Olah, G. A., Ed.;
Interscience: New York, NY, 1964; Vol. 3, pp 911–1002; (d)
Gore, P. H. Chem. Rev. 1955, 55, 229–281; (e) Johnson,
W. S. Org. React. 1944, 2, 114–177.
3. (a) Sasski, T.; Eguchi, S.; Yamada, S.; Hioki, T. J. Chem. Soc.,
Perkin Trans. 1 1982, 1953–1958; (b) Johnston, K. M.; Shotter,
R. G. Tetrahedron 1974, 30, 4059–4064; (c) Gold, A.; Schultz,
J.; Eisenstadt, E. Tetrahedron Lett. 1978, 19, 4491–4494;
(d) Zhang, W.; Cao, X.; Zi, H.; Pei, J. Org. Lett. 2005, 7,
959–962.
Jones reagent dropwise until the color of solution became or-
ange. The reaction mixture was stirred for 30 min at 0 ꢀC and
subsequently monitored by TLC. After completion of reac-
tion as monitored by TLC (EtOAc/hexane, 6:1), 10 mL of
water was added, followed by the addition of 10 mL of di-
ethyl ether. The organic layer was separated, whereas the
aqueous layer was further extracted with 3ꢂ10 mL portions
of diethyl ether. After evaporation, the crude product 7a was
purified by column chromatography using ethyl acetate/
hexane (1:6) as eluent. Yield: 90%; mp: 67–69 ꢀC; IR:
1
1717 cmꢁ1; H NMR (CDCl3): d 0.88 (t, 3H, J¼7.2 Hz),
1.31 (m, 2H), 1.53 (m, 2H), 2.58 (t, 2H, J¼7.6 Hz), 2.66
(t, 2H, J¼6.2 Hz), 2.99 (t, 2H, J¼6.2 Hz), 7.14 (s, 1H),
7.28 (s, 1H); 13C NMR (CDCl3): d 13.8, 22.2, 24.7, 33.0,
35.4, 37.0, 119.1, 125.5, 132.0, 132.6, 151.5, 158.0, 203.3;
Mass calculated for (M+) C13H15BrO: 266.0306, found
(HRMS-EI): 266.0307.
4. (a) Cullinane, N. M.; Chard, S. J.; Leyshon, D. M. J. Chem. Soc.
1952, 4106–4108; (b) Baddeley, G.; Voss, D. J. Chem. Soc.
1954, 418–422; (c) Satchell, D. P. N. J. Chem. Soc. 1961,
5404–5415; (d) Melvyn, G. Tetrahedron 1984, 40, 621–626.
5. (a) Popp, F. D.; McEwen, W. E. Chem. Rev. 1958, 58, 321–401;
(b) Guy, A.; Guette, J. Synthesis 1980, 222–223; (c) Braun, M.
Tetrahedron 1984, 40, 4585–4591.
6. Premasagar, V.; Palaniswamy, V. A.; Eisenbraun, E. J. J. Org.
Chem. 1981, 46, 2974–2976.
7. (a) Posner, G. H.; Chapdelaine, M. J.; Lentz, C. M. J. Org.
Chem. 1979, 44, 3661–3665; (b) Fieser, F.; Hershberg, E. B.
J. Am. Chem. Soc. 1939, 61, 1272.
Acknowledgements
This work was financially supported by US Department
of Energy (Grant DE-FG02-05ER46238). Mass spectra
were obtained at the Mass Spectrometry Laboratory for
Biotechnology at North Carolina State University. Partial
funding for the facility was obtained from the North
Carolina Biotechnology Center and the National Science
Foundation.
8. (a) Perkin, W. H.; Robinson, R. J. Chem. Soc. 1907, 91, 1073–
1103; (b) Johnson, W. S.; Glenn, H. J. J. Am. Chem. Soc. 1949,
71, 1092–1096.
Supplementary data
9. Ragan, J. A.; Murry, J. A.; Castaldi, M. J.; Conrad, A. K.; Jones,
B. P.; Li, B.; Makowski, T. W.; McDermott, R.; Sitter, B. J.;
White, T. D.; Young, G. R. Org. Process Res. Dev. 2001, 5,
498–507.
1H and 13C spectra for all products. Supplementary data as-
sociated with this article can be found in the online version,
10. (a) Yamato, T.; Hideshima, C.; Prakash, G. K.; Olah, G. A.
J. Org. Chem. 1991, 56, 3955–3957; (b) Olah, G. A.; Mathew,
T.; Farnia, M.; Prakash, G. K. Synlett 1999, 1067–1068.
11. (a) Matveeva, E. D.; Podrugina, T. A.; Morozkina, N. Y.;
Zefirova, O. N.; Seregin, I. V.; Bachurin, S. O.; Pellicciari,
R.; Zefirov, N. S. Russ. J. Org. Chem. 2002, 38, 1769–1774;
(b) Adamczyk, M.; Watt, D. S.; Daniel, A.; Netzel, D. A.
J. Org. Chem. 1984, 49, 4226–4237; (c) Musso, D. L.;
Cochran, F. R.; Kelley, J. L.; McLean, E. W.; Selph, J. L.;
Rigdon, G. C.; Orr, G. F.; Davis, R. G.; Cooper, B. R.;
Styles, V. L.; Thompson, J. B.; Hall, W. R. J. Med. Chem.
2003, 46, 399–408; (d) Brown, D. S.; Brian, A.; Marples,
B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587–
3606.
References and notes
1. For biological importance of indanones, see: (a) Hanna, G. M.;
Lau-cam, C. A. J. Pharm. Biomed. Anal. 1989, 7, 919–928 and
references cited therein; (b) Field, M. J.; Fowler, N.; Giebisch,
G. H. J. Pharmacol. Exp. Ther. 1984, 230, 62–68; (c) Ioav,
C. Z.; Shirley, K.; Miriam, K.; Hagai, G. Mol. Pharmacol.
1983, 23, 92–99; (d) Mithofer, A.; Maitrejean, M.; Boland,
M. J. Plant Growth Regul. 2005, 23, 170–178; (e) Leoni,
L. M.; Hamel, E.; Genini, D.; Shih, H.; Carrera, C. J.;
Cottam, H. B.; Dennis, A.; Carson, D. A. J. Natl. Cancer
Inst. 2000, 92, 217–224; (f) Pinkerton, A. B.; Cube, R. V.;
Hutchinson, J. H.; James, J. K.; Gardner, M. F.; Rowe, B. A.;
Schaffhauser, H.; Rodriguez, D. E.; Campbell, U. C.;
Daggett, L. P.; Vernier, J. Bioorg. Med. Chem. Lett. 2005, 15,
1565–1571; (g) Klein, T.; Niising, R. M.; Wiesenberg-
Boettcher, I.; Ullrich, V. Biochem. Pharmacol. 1996, 51,
285–290; (h) Chun-Sing, L.; Black, W. C.; Chan, C.; Ford-
Hutchinson, A. W.; Gauthier, J.; Gordon, R.; Guay, D.;
Kargman, S.; Lau, C. K.; Mancini, J.; Ouimet, N.; Roy, P.;
Vickers, P.; Wong, E.; Young, R. N.; Zamboni, R.; Prasit, P.
J. Med. Chem. 1995, 38, 4897–4905; (i) Yamamoto, Y.;
Ishihara, Y.; Kuntz, I. D. J. Med. Chem. 1994, 37, 3141–
3153; (j) Biggs, D. F.; Casy, A. F.; Chu, I.; Coutts, R. T.
ꢀ
€ ꢀ
12. Toth, G.; Kover, K. E. Synth. Commun. 1995, 25, 3067–
3074.
13. Helavi, V. B.; Solabannavar, S. B.; Desai, U. V.; Mane, R. B.
J. Chem. Res., Synop. 2003, 174–175.
14. Fillion, E.; Fishlock, D. Org. Lett. 2003, 5, 4653–4656.
15. Fillion, E.; Fishlock, D.; Wilsily, A.; Goll, J. M. J. Org. Chem.
2005, 70, 1316–1327.
16. Panetta, C. A.; Sha, D.; Torres, E.; He, Z.; Hussey, C. L.; Fang,
Z.; Heimer, N. E. Synthesis 1997, 1085–1090.
17. Nguyen, P.; Corpuz, E.; Todd, M.; Heidelbaugh, T. M.;
Chow, K.; Garst, M. E. J. Org. Chem. 2003, 68, 10195–
10198.