J. Jacobs et al. / Tetrahedron Letters 50 (2009) 3698–3701
Haloaldehydes and
3701
a
-Haloimines; Patai, S., Rappoport, Z., Eds.; John Wiley &
References and notes
Sons: New York, 1988; p 279.
11. Cannon, J. G.; Webster, G. L. J. Am. Pharm. Assoc. Sci. Ed. 1958, 47, 353–355.
12. (a) Bhattacharjya, A.; Chattopadhyay, P.; Bhaumik, M.; Pakrashi, S. C. J. Chem.
Res. 1989, 228–229; (b) Zhao, B. X.; Yu, Y.; Eguchi, S. Org. Prep. Proced. Int. 1997,
29, 185–194.
13. (a) De Kimpe, N.; Verhé, R.; De Buyck, L.; Schamp, N. Synth. Commun. 1975, 5,
269–274; (b) Verhé, R.; De Kimpe, N.; De Buyck, L.; Schamp, N. Synthesis 1975,
455–456; (c) De Kimpe, N.; Verhé, R.; De Buyck, L.; Schamp, N. J. Org. Chem.
1978, 43, 2933–2935; (d) De Kimpe, N.; Verhé, R.; De Buyck, L.; Tukiman, S.;
Schamp, N. Tetrahedron 1979, 35, 789–798.
1. (a) Kametani, T. The Total Syntheses of Isoquinoline Alkaloids. In The Total
Synthesis of Natural Products; Apsimon, J., Ed.; John Wiley: New York, 1977; Vol.
3, pp 1–127; (b) Alvarez, M.; Joule, J. A. Isoquinolines. In Science of Synthesis;
Black, D., Ed.; Thieme: Germany, 2005; Vol. 15, pp 661–838.
2. Bjorklund, J. A.; Frenzel, T.; Rueffer, M.; Kobayashi, M.; Mocek, U.; Fox, C.; Beale,
J. M.; Gröger, S.; Zenk, M. H.; Floss, H. G. J. Am. Chem. Soc. 1995, 117, 1533–1545.
3. Hoye, T. R.; Chen, M. Z.; Hoang, B.; Mi, L.; Priest, O. P. J. Org. Chem. 1999, 64,
7184–7201.
4. Nawrath, H. J. Pharmacol. Exp. Ther. 1981, 218, 544–549.
14. Pawallek, D.; Bradsher, C. K. J. Org. Chem. 1960, 25, 281–282.
15. All new compounds were fully characterized on the basis of IR, MS, 1H NMR,
and 13C NMR spectroscopy. Spectral data of selected compounds can be found
below. Compound 3a: Colorless oil (purity >95%), no purification due to
decomposition of the compound on silica gel; 1H NMR (270 MHz, CDCl3): d
2.63 (2H, t, J = 7.5 Hz, H-4), 3.74 (2H, t, J = 7.5 Hz, H-3), 6.56 (1H, s, CHCl2),
6.91–7.49 (3H, m, 3 Â CH@), 7.69–7.81 (1H, m, CH@); 13C NMR (68 MHz,
CDCl3): d 25.5 (C-4), 47.0 (C-3), 71.1 (CHCl2), 124.1 (@Cquat), 126.2 (CH@), 126.6
(CH@), 127.9 (CH@), 131.6 (CH@), 138.3 (@Cquat), 162.0 (C-1); IR (NaCl): mmax
1621 cmÀ1; MS m/z (%): 213/215/217 (M+, 33), 178/180 (100), 151 (10), 150
(6), 149 (10). Compound 5a: Colorless oil, purification by flash chromatography
on silica gel; 1H NMR (270 MHz, CDCl3): d 3.38 (3H, s, OMe), 4.96 (2H, s,
CH2OMe), 7.29–7.70 (4H, m, 3 Â CH@ and H-4), 8.01–8.39 (1H, m, CH@), 8.41
(1H , d, J = 5.8 Hz, H-3); 13C NMR (68 MHz, CDCl3): d 58.3 (OMe), 75.0 (CH2O),
120.9 (CH@), 125.5 (CH@), 127.0 (CH@), 127.1 (CH@), 127.2 (@Cquat), 129.9
(CH@), 136.3 (@Cquat), 141.6 (CH@), 157.0 (C-1); IR (NaCl): mmax 1622, 1582,
1560, 1450, 1189, 1100 cmÀ1; MS m/z (%): no M+, 149 (6), 146 (6), 115 (13), 43
(100). Anal. Calcd for C11H11NO: C, 76.28; H, 6.40; N, 8.09. Found: C, 76.46; H,
6.58; N, 7.88.
5. Masaki, N.; Lizuka, H.; Yokota, M.; Ochiai, A. J. Chem. Soc., Perkin Trans. 1 1977,
717–719.
6. Kametani, T.; Honda, T. Alkaloids 1985, 24, 153–251.
7. Nair, M. D.; Premila, M. S. In Halogenated and Metallated Isoquinolines and Their
Hydrogenated Derivatives in the Chemistry of Heterocyclic Compounds
(Isoquinolines Part 2); Kathawalla, F. G., Coppola, G. M., Schuster, H. F., Eds.;
John Wiley & Sons: New York, 1990; pp 1–533.
8. (a) Atanes, N.; Castedo, L.; Cobas, A.; Guitian, E.; Saa, C.; Saa, J. M. Tetrahedron
1989, 45, 7947–7956; (b) Orito, K.; Miyazawa, M.; Suginome, H. Synlett 1994,
245–246; (c) Venkov, A. P.; Statkova, S. M. Synth. Commun. 1991, 21, 1511–
1520; (d) Georgieva, A.; Stanoeva, E.; Spassov, S.; Macicek, J.; Angelova, O.;
Haimova, M.; De Kimpe, N. Tetrahedron 1991, 47, 3375–3388.
9. Whaley, W. M.; Govindachari, T. R. Org. React. 1951, 6, 74–150.
10. (a) De Kimpe, N.; Verhé, R.; De Buyck, L.; Schamp, N. J. Org. Chem. 1980, 45,
5319–5325; (b) De Kimpe, N.; Verhé, R.; De Buyck, L.; Schamp, N. Org. Prep.
Proced. Int. 1980, 12, 49–180; (c) De Kimpe, N.; Sulmon, P.; Verhé, R.; De Buyck,
L.; Schamp, N. J. Org. Chem. 1983, 48, 4320–4326; (d) De Kimpe, N.; Sulmon, P.;
Moëns, L.; Schamp, N.; Declercq, J. P.; Van Meerssche, M. J. Org. Chem. 1986, 51,
3839–3848; (e) De Kimpe, N.; Verhé, R. In The Chemistry of
a-Haloketones, a-