2-(4-Chlorophenyl)-1,2-dihydronaptho[1,2-f][1,4]oxazepin-3(4H)-one 7c. Yield: 72%. mp: 133 °C. IR (KBr) •max: 1656, 1615-1495, 1242 cm-1. UV (EtOH) •max(log •): 388.0 (0.017), 314.4 (0.065), 278.8 (0.202), 259.2 (0.997) nm. 1H-NMR (400 MHz, CDCl3) •: 4.82 (2H, s, - CH2-O), 5.20 (2H, s, -CH2-N), 7.12 (2H, d, J=8.0 Hz, 3•N•-H), 7.30 (1H, d, J=8.8 Hz, 3-H), 7.31 (2H, d, J=8.0 Hz, 2•N•-H), 7.37 (1H, t, J=8.4 Hz, 6-H), 7.48 (1H, t, J=6.8 Hz, 7-H), 7.70 (1H, d, J=8.4 Hz, 4-H), 7.79 (1H, d, J=8.4 Hz, 5-H), 7.81 (1H, d, J=7.1 Hz, 8-H). 13C-NMR (100 MHz, CDCl3) •: 47.1 (Ar-CH2-N), 73.3 (O-CH2), 120.4 (3-C), 122.2 (8-C), 122.5 (2•N•-C), 125.4 (6-C), 127.9 (7-C), 130.1 (4-C), 130.1 (5-C), 130.8 (4a-C), 131.2 (8a-C), 131.4 (3•N•-C), 133.5 (4•N•-C), 142.9 (1•N•-C), 156.5 (2-C), 169.5 (C=O). MS: m/z 323 (M+). Anal. Calcd. for C19H14ClNO2 (323.77): C, 70.48; H, 4.36; N, 4.33. Found: C, 70.31; H, 4.69; N, 4.34. Acknowledgements This work was supported by the Eskisehir Osmangazi University Scientific Research Project Commission (Grant No. 200419036). References 1. Schenker, K. Swiss Patent 505 850, 1971. 2. Toshiyuki, H.; Takahiro, I.; Hisao, Y. Ger. Offen. 2 014 223, 1969. 3. Standridge, R. T. U.S. Patent 4 125 538, 1978; Chem. Abstr. 1979, 90, 72246r. 4. Liao, Y.; Venhuis, B. J.; Rodenhuis, N.; Timmerman, W.; Wikström, H.; Meier, E.; Bartoszyk, G. D.; Böttcher, H.; Seyfried, C. A.; Sundell, S. J. Med. Chem. 1999, 42, 2235. 5. Nagarajan, K.; Venkateswarlu, A.; Kulkarni C. L.; Nagana, G. A.; Shah, R. K. Indian J. Chem. 1974, 12, 236. 6. Nagarajan, K.; David, J.; Kulkarn, Y. S.; Hendi, S. B.; Shenoy, S. J.; Upadhyaya, P. Eur. J. Med. Chem. 1986, 21, 21. 7. Lee, J.; Gauthier, D.; Rivero, D. A. J. Org. Chem. 1999, 64, 3060. (b) Kraus, G. A.; Liu, P. Tetrahedron Lett. 1995, 36, 7595. 8. Levy, O.; Erez, M.; Varon, D.; Keinan, E. Bioorg. Med. Chem. Lett. 2001, 11, 2921. (b) Cohen, V. I.; Jin, B.; Cohen, E. I.; Zeeberg, B. R. J. Heterocycl. Chem. 1998, 35, 675. 9. Klunder, J. M.; Hargrave, K. D.; West, M.; Cullen, E.; Pal, K.; Behnke, M. L.; Kapadia, S. R.; McNeil, D. W.; Wu, J. C.; Chow, G. C. J. Med. Chem. 1992, 35, 1887. (b) Aiello, F.; Brizzi, A.; Garofalo, A.; Grande, F.; Ragno, G.; Dayam, R.; Neamati, N. Bioorg. Med. Chem. 2004, 12, 4459. 10. Pecher, J.; Waefelaer, A.; Poultier, P. Bull. Soc. Chim. Belg. 1977, 86, 1003. (b) Pecher, J.; Waefelaer, A. Bull. Soc. Chim. Belg. 1978, 87, 911. 11. Heaney, H.; Shuhaibar, K. F. Tetrahedron Lett. 1994, 35, 2751. 12. El Gihani, M. T.; Heaney, H.; Shuhaibar, K. F. Synlett. 1996, 871.
Top of page Top of page