J. G. Avila-Za´rraga et al. / Tetrahedron Letters 47 (2006) 7987–7989
7989
Chem. 1999, 42, 2909; (b) Kunick, C.; Laurenroth, K.;
Wieking, K.; Xie, X.; Schultz, C.; Gussio, R.; Zaharevitz,
D.; Leost, M.; Meijer, L.; Weber, A.; Jorgensen, F. S.;
Lemcke, T. J. Med. Chem. 2004, 47, 22.
12. Bremner, J. B.; Sengpracha, W. Tetrahedron 2005, 61,
5489.
13. Selected spectral data. Compound 4: IR (film): 3054, 3024,
1666, 1651, 1583, 1476, 1373, 129, 740 cmÀ1 1H NMR
.
2. (a) Zaharevitz, D. W.; Gussio, R.; Leost, M.; Sendero-
wickz, A. M.; Lahusen, T.; Kunick, C.; Meijer, L.;
Sausville, E. A. Cancer Res. 1999, 59, 2566; (b) Ling, R.;
Yoshida, M.; Mariano, P. S. J. Org. Chem. 1996, 61, 4439.
3. (a) Meijer, L.; Flajolet, M.; Greengard, P. Trends Phar-
macol. Sci. 2004, 25, 471; (b) Knockaert, M.; Wieking, K.;
Schmitt, S.; Leost, M.; Grant, K. M.; Mottram, J. C.;
Kunick, C.; Meijer, L. J. Biol. Chem. 2002, 277, 25493; (c)
Leost, M.; Schultz, C.; Link, A.; Wu, Y.; Biernat, J.;
Mandelkow, E.; Bibb, J. A.; Gretchen, L. S.; Greengard,
P.; Zaharevitz, D. W.; Gussio, R.; Senderowicz, A. M.;
Sausville, E. A.; Kunick, C.; Meijer, L. Eur. J. Biochem.
2000, 267, 5983.
4. Kunick, C.; Schultz, C.; Lemcke, T.; Zaharevitz, D. W.;
Gussio, R.; Jalluri, R. K.; Sausville, E. A.; Leost, M.;
Meijer, L. Biorg. Med. Chem. Lett. 2000, 10, 567.
5. Sielecki, T. M.; Boylan, J. F.; Benfield, P. A.; Trainor, G.
L. J. Med. Chem. 2000, 43, 1.
6. (a) Kozikowski, A. P.; Ma, D.; Romeo, E.; Auta, J.;
Papadopoulos, V.; Puia, G.; Costa, E.; Guidotti, A.
Angew. Chem., Int. Ed. Engl. 1992, 31, 1060; (b) Kozi-
kowski, A. P.; Ma, D.; Brewer, J.; Sun, S.; Costa, E.;
Romeo, E.; Guidotti, A. J. Med. Chem. 1993, 36, 2908.
(300 MHz, CDCl3) d 7.69 (dd, J = 1.5/7.8 Hz, 1H), 7.34–
7.14 (m, 4 H), 7.04 (d, J = 1.2 Hz, 1H), 7.01 (t, J = 1.2 Hz,
1H), 6.99 (d, J = 1.2 Hz, 1H), 6.85 (s, 1H), 3.71 (s, 3H),
3.51 (br s, 1H), 3.50 (br s, 1H), 3.22 (s, 3H); 13C NMR
(75.5 MHz, CDCl3) d 166.10, 142.92, 136.70, 133.80,
130.14, 129.63, 128.78, 127.78, 123.58, 121.39, 118.88,
118.79, 108.96, 107.50, 36.10, 32.57, 30.85. MS, m/z (%)
M+ 356 (42), M++2 358 (41), 144 (100), 143 (27). HRMS
m/z for C18H17ON2Br. Calcd: 356.0524, found: 356.0524.
1
Compound 2: IR (film): 1660, 1469, 1371, 1115, 742. H
NMR (400 MHz, CDCl3) d 7.74 (dt, J = 0.8/0.8/8 Hz,
1H), 7.55 (dd, J = 2/8 Hz, 1H), 7.48–7.28 (m, 5H), 7.2 (t,
J = 7.2 Hz, 1H), 3.96 (d, J = 14.4 Hz, 1H), 3.90 (s, 3H),
3.35 (s, 3H), 3.06 (d, J = 14 Hz, 1H); 13C NMR
(100 MHz, CDCl3) d 172.82, 141.69, 139.17, 133.66,
128.51, 127.94, 125.59, 124.98, 124.62, 124.22, 122.75,
119.97, 118.68, 112.31, 109.68, 37.61, 32.24, 31.75. MS,
m/z (%) M+ 276 (75), 261 (68), 247 (100), 232 (20), 117
(19). HRMS m/z for C18H16ON2. Calcd: 276.1263, found:
276.1264.
´
´
14. Avila-Zarraga, J. G.; Martınez, R. Synth. Commun. 2001,
31, 2177.
15. Escolano, C.; Jones, K. Tetrahedron 2002, 58, 1453.
16. For a review about Heck reaction see: (a) Beletskaya, P.;
Cheprako, A. V. Chem. Rev. 2000, 100, 3009; (b) Kozi-
kowski, A. P.; Ma, D. Tetrahedron Lett. 1991, 32, 3317; (c)
Yao, Q.; Kinney, E. P.; Yang, Z. J. Org. Chem. 2003, 68,
7528; (d) Kim, G.; Kim, J. H.; Lee, K. J. Org. Chem. 2006,
71, 2185.
17. Lane, B. S.; Sames, D. Org. Lett. 2004, 6, 2897.
18. Joucla, L.; Putey, A.; Benoit, J. Tetrahedron Lett. 2005,
46, 8177.
´
7. Baudoin, O.; Cesario, M.; Guenard, D.; Gueritte, F. J.
Org. Chem. 2002, 67, 1199.
8. Bonner, W. A.; McNamee, P. I. J. Org. Chem. 1961, 26,
2554.
9. Ganguly, A. K.; Wang, C. H.; David, M.; Bartner, P.;
Chan, T. M. Tetrahedron Lett. 2002, 43, 6865.
10. Miwako, M.; Shigeko, N.; Yoshio, B. Tetrahedron Lett.
1973, 49, 4951.
11. (a) Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219,
211; (b) Sezen, B.; Sames, D. J. Am. Chem. Soc. 2003, 125,
5274.
19. Julia, M.; Tchernoff, G. Bull. Chem. Soc. Fr. 1960, 741.