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Venkateswarlu, Y.; Faulkner, D. J. J. Med. Chem. 1999, 42,
1901. (d) Chawla, A. S.; Kapoor, V. K. In Pelletier, S. W., Ed.;
Alkaloids: Chemical and Biological Prospectives; 1995, 86.
3. (a) Schultes, R. E.; Raffauf, D. The Healing Forest. Medicinal
and Toxic Plants of the Northwest Amazonia; R. F.
Dioscorides, 1990; See also the references cited therein. (b)
Amer, M. E.; Shamma, M.; Freyer, A. J. J. Nat. Prod. 1991,
54, 329 and references cited therein. (c) Dyke, S. F.; Quessy,
S. N. In Rodrigo, R. G. A., Ed.; The Alkaloids; Academic:
New York, 1981; Vol. 18.
(CDCl3, 75 MHz) d 57.8, 123.4, 123.9, 124.2, 124.6, 125.6,
126.9, 128.5, 128.6, 128.7, 129.2, 129.3, 132.1, 132.5, 134.5,
172.1; MS (EI): m/zZ233 [MC]. Anal. Calcd for C16H11NO
(233.08): C, 82.38; H, 4.75; N, 6.00. Found. C, 82.21; H,
4.66; N, 5.86.
4.9.2. 12b,13-Dihydrobenzo[4,5]azepino[2,1-a]isoind-ol-
8-one (5b). This product was isolated as a white-yellow
solid in yields indicated above; mpZ110 8C (ethanol); IR
(KBr) y~maxZ3012 (CH), 1701 (C]O) cmK1 1H NMR
;
(CDCl3, 300 MHz) d 3.05 (dd, 1H, JZ14.1, 7.0 Hz,
CH2–CH), 3.51 (dd, 1H, JZ14.1, 3.1 Hz, CH2–CH), 5.08
(dd, 1H, JZ7.0, 3.1 Hz, CH–CH2), 6.10 (d, 1H, JZ14.1 Hz,
CH]CH), 6.88–6.93 (m, 2H, aromatic), 7.05–7.52 (m, 6H,
CH]CHCaromatic), 7.74 (d, 1H, JZ7.0 Hz, aromatic);
13C NMR (CDCl3, 75 MHz) d 42.0, 60.6, 109.9, 121.4,
122.4, 124.3, 127.0, 127.4, 129.0, 129.9, 130.8, 131.2,
133.0, 135.4, 135.9, 144.4, 165.8; MS (EI): m/zZ247 [MC].
Anal. Calcd for C17H13NO (247.10): C, 82.38; H, 4.75; N,
6.00. Found. C, 82.21; H, 4.66; N, 5.86.
4. (a) Shamma, M. In The Protoberberines and Retro-Protober-
berines; Blomquist, A. T., Wasserman, H., Eds.; The
Isoquinoline Alkaloids: Chemistry and Pharmacology;
Academic: New York, 1972; Vol. 25, p 268. (b) Shamma,
M.; Moniot, J. Isoquinoline Alkaloids Research; Plenum: New
York, 1978. (c) Shamma, M.; Rahimizadeh, M. J. Nat. Prod.
1986, 49, 398. (d) Bentley, K. W. The Berberines and
Tetrahydroberberines. In Ravindranath, B., Ed.; The Isoquino-
line Alkaloids: Chemistry and Pharmacology; Harwood
Academic: Bangalore, 1988; Vol. 1, p 219.
5. (a) Sorgi, K. L.; Maryanoff, C. A.; McComsey, D. F.; Graden,
D. W.; Maryanoff, B. E. J. Am. Chem. Soc. 1990, 112, 3567.
(b) Maryanoff, B. E.; McComsey, D. F.; Mutter, M. S.; Sorgi,
K. L.; Maryanoff, C. A. Tetrahedron Lett. 1988, 29, 5073.
6. (a) Zhang, Q.; Tu, G.; Zhao, Y.; Cheng, T. Tetrahedron 2002,
4.9.3. (cis and trans)-5,12b-Dihydro-5-phenylthioiso-
indolo[1,2-a]isoquinolin-8(6H)-one (16a). Following a
procedure similar to that described above for the preparation
of cyclic isoindolines 5a,b, the sulfide 16a as the Pummerer
type-cyclization intermediate was isolated when the
reaction was performed at room temperature for 30 min.
After a similar work-up as above, this product, 16a, was
obtained as a mixture of two diastereomers in 56/44 ratio as
uncolourless oil in quantitative yield; IR (neat) y~maxZ3016
¨
58, 6795. (b) Knolker, H.-J.; Agarwal, S. Tetrahedron Lett.
2005, 46, 1173.
7. (a) Juma, B. F.; Majinda, R. R. T. Phytochemistry 2004, 65,
1397. (b) See also Ref. 3b.
8. Ito, K.; Haruna, M.; Jinno, Y.; Furukawa, H. Chem. Pharm.
Bull. 1976, 24, 52.
1
and 2983 (CH), 1704 (C]O) cmK1; H NMR (CDCl3,
300 MHz) d 3.18 (dd, 1H, JZ14.1, 9.4 Hz, CH2–CHS,
major isomer), 3.32 (dd, 1H, JZ14.1, 5.5 Hz, CH2–CHS,
minor isomer), 4.31 (dd, 1H, JZ14.1, 3.9 Hz, CH2–CHS,
major isomer), 4.44 (dd, 1H, JZ14.1, 5.5 Hz, CH2–CHS,
minor isomer), 4.48 (s, 1H, CH, major isomer), 5.67 (s, 1H,
CH, minor isomer), 6.33 (dd, 1H, JZ9.4, 3.9 Hz,
SCH–CH2, major isomer), 6.47 (d, 1H, JZ5.5 Hz,
SCH–CH2, minor isomer), 6.97–7.41 (m, 2!13H,
aromatic, mixture), 7.83–7.96 (m, 2!1H, aromatic,
mixture); MS (EI): m/zZ233 [MCKPhSH].
9. Tsuda, Y.; Hosoi, S.; Nakai, A.; Ohshima, T.; Sakai, Y.;
Kiuchi, F. J. Chem. Soc., Chem. Commun. 1984, 1216.
¨
10. Jousse, C.; Desmaele, D. Eur. J. Org. Chem. 1999, 909.
11. (a) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P.
J. Org. Chem. 2002, 67, 9464. (b) Allin, S. M.; Streetley, G. B.;
Slater, M.; James, S. L.; Martin, W. P. Tetrahedron Lett. 2004,
45, 5493.
12. Toda, J.; Niimura, Y.; Sano, T.; Tsuda, Y. Heterocycles 1998,
48, 1599 and the references cited therein.
13. Kessar, S. V.; Singh, T.; Vohra, R. Tetrahedron Lett. 1987, 28,
5323.
14. Mazzocchi, P. H.; King, C. R.; Ammon, H. L. Tetrahedron
Lett. 1987, 28, 2473.
Acknowledgements
15. (a) Ishibashi, H.; Kawanami, H.; Iriyama, H.; Ikeda, M.
Tetrahedron Lett. 1995, 36, 6733. (b) Ishibashi, H.;
Kawanami, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1
1997, 6817.
The authors are grateful for many helpful comments and
fruitful discussions throughout the course of this work with
Professor Bernard Decroix. The authors also thank the
Scientific Council of University of Le Havre, France, for
their support of this research program.
¨
16. Hucher, N.; Decroix, B.; Daıch, A. J. Org. Chem. 2001, 66,
4695.
¨ ¨
17. Hucher, N.; Pesquet, A.; Netchitaılo, P.; Daıch, A. Eur. J. Org.
Chem. 2005, 2758.
¨
18. Cul, A.; Daıch, A.; Decroix, B.; Sanz, G.; Van Hijfte, L.
Heterocycles 2004, 64, 33.
¨
19. Hucher, N.; Daıch, A.; Decroix, B. Org. Lett. 2000, 2, 1201.
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