3-Substituted Isochromen-1-ones
3655
2.53 (t, J ¼ 7.52 Hz, 2H), 1.74–1.66 (m, 2H), 1.46–1.36 (m, 2H), 0.95
(t, J ¼ 7.52 Hz, 3H). 13C NMR (CDCl3): d 158.3, 137.7, 135.9, 134.7,
130.1, 129.5, 127.5, 123.0, 102.9, 37.6, 28.9, 22.1, 13.7.
3-Cyclohexenylisocoumarin (3g)
IR (KBr) (cm21): 2978, 1695, 1657. 1H NMR (CDCl3): d 8.20–8.18 (m, 1H),
7.62–7.59 (m, 1H), 7.39–7.34 (m, 1H), 6.78 (d, J ¼ 7.8 Hz, 1H), 6.31 (s, 1H),
2.27–2.24 (m, 2H), 2.23–2.13 (m, 2H), 1.76–1.59 (m, 5H). 13C NMR
(CDCl3): d 163.5 137.76, 134.63, 129.45, 127.48, 125.23, 120.28, 100.88,
41.68, 30.58, 25.94, 25.88.
The spectral and C, H, N data of these compounds were reported pre-
viously,[12] and our results have been compared for authenticity.
ACKNOWLEDGMENT
The authors express their gratitude to the Indian Institute of Science, sophicas-
ticated analytical instruments facility (SAIF), Bangalore, and Spic Science
Foundation, Tuticorin, for NMR spectra.
REFERENCES
1. Matsuda, H.; Shimoda, H.; Yoshikawa, M. Bioorg. Med. Chem. 1999, 7,
1445–1450.
2. Yoshikawa, M.; Harada, E.; Naitoh, Y.; Inoue, K.; Matsuda, H.; Shimoda, H.;
Yamahara, J.; Murakami, N. Chem. Pharm. Bull. 1994, 42, 2225–2230.
3. (a) Matsuda, H.; Shimoda, H.; Yamahara, J.; Yoshikawa, M. Bioorg. Med. Chem.
Lett. 1998, 8, 215–220; (b) Shimoda, H.; Matsuda, H.; Yamahara, J.;
Yoshikawa, M. Biol. Pharm. Bull. 1998, 21, 809–813.
4. Whyte, A. C.; Gloer, J. B.; Scott, J. A.; Mallock, D. J. Nat. Prod. 1996, 59,
765–769.
5. Nozawa, K.; Yamada, M.; Tsuda, Y.; Kawai, K.; Nakajima, S. Chem. Pharm. Bull.
1981, 29, 2689–2691.
6. Furuta, T.; Fukuyama, Y.; Asakawa, Y. Phytochemistry 1986, 25, 517–520.
7. Lee, J. H.; Park, Y. J.; Kim, H. S.; Hong, Y. S.; Kim, K.- W.; Lee, J. J. J. Antibiot.
2001, 54, 463–466.
8. (a) Barry, R. D. Chem. Rev. 1964, 64, 229–260; (b) Houser, F. M.;
Baghdanov, V. M. J. Org. Chem. 1988, 53, 4676–4681; (c) Mali, R. S.;
Babu, K. N. J. Org. Chem. 1998, 63, 2488–2492, and references cited therein.
9. (a) Jones, J. B.; Pinder, A. R. J. Chem. Soc. 1958, 2612–2618; (b) Tirodkar, R. B.;
Usgaonkar, R. N. Indian J. Chem. 1972, 10, 1060–1064.
10. For a review, see Napolitano, E. Org. Prep. Proced. Int. 1997, 29, 631–664.
11. (a) Izumi, T.; Morishita, N. J. Heterocycl. Chem. 1994, 31, 145–152; (b) Ohta, S.;
Kamata, Y.; Inagaki, T.; Masuda, Y.; Yamamoto, S.; Yamashita, M.; Kawasaki, I.