Chapter 6 Synthesis of benzodiazepines IR spectrum of compound ADZ-03 100 %T 80 60 40 20 3182.65 3120.93 3068.85 2955.04 2899.11 1610.61 1504.53 1479.45 1429.30 1406.15 1367.58 1317.43 1288.49 1232.55 1153.47 1097.53 1024.24 945.15 839.06 810.13 761.91 731.05 690.54 665.46 586.38 0 1693.56 1672.34 -20 4000 3500 3000 2500 2000 1750 1500 1250 1000 750 500 1/cm IR spectrum of compound ADZ-05c 105 %T 90 3232.80 3070.78 2997.48 2906.82 2833.52 943.22 75 1481.38 1419.66 1363.72 1319.35 1155.40 1138.04 1026.16 731.05 690.54 60 1608.69 1591.33 1506.46 1265.35 848.71 802.41 630.74 45 1683.91 1670.41 761.91 557.45 538.16 480.29 30 518.87 453.29 441 71 15 4000 3500 3000 2500 2000 1750 1500 1250 1000 750 500 1/cm Department of Chemistry, <strong>Saurashtra</strong> <strong>University</strong>, Rajkot-360005 230
Chapter 6 Synthesis of benzodiazepines 6.9 References 1. Rohtash, K.; Lown, J. W.; Mini-Reviews in Medicinal Chemistry, 2003, 3, 323. 2. Bertelli, L.; Biagi, G.; Giorgi, I.; Livi, O.; Manera, C.; Scartoni, V.; Martini, C.; Giannaccini, G.; Trincavelli, L.; Barilli, P.L.; IlFarmaco., 1998, 53, 305. 3. Balakrishna, M. S.; Kaboudin, B.; Tetrahedron Lett., 2001, 42, 1127. 4. Lattmann, E.; Sattayasai, J.; Billington, D. C.; Poyner, D. R.; Puapairoj, P.; Tiamkao, S.; Airarat, W.; Singh, H.; Offel, M.; J. Pharmacy and Pharmacology., 2002, 54, 827. 5. Bertelli, L.; Biagi, G.; Giorgi, I.; Livi, O.; Manera, C.; Scartoni, V.; Martini, C.; Giannaccini, G.; Trincavelli, L.; Barili, P.L.; Farmaco., 2000, 53, 305. 6. Schutz, H.; Benzodiazepines; Springer: Heidelberg, Germany, 1982. 7. Randall, L. O.; Kamel, B.; In Benzodiazepines; Garattini, S.; Mussini, E.; Randall, L. O.; Eds.; Raven Press: New York, 1973, 27. 8. De Baun, J. R.; Pallos, F. M.; Baker, D. R.; U.S. Patent 3, 978, 227, 1976, Chem. Abstr.,1977, 86, 5498d. 9. Merluzzi, V.; Hargrave, K. D.; Labadia, M.; Grozinger, K.; Skoog, M.; Wu, J. C.; Shih, C. K.; Eckner, K.; Hattox, S.; Adams, J.; Rosenthal, A. S.; Faanes, R.; Eckner, R. J.; Koup, R. A.; Sullivan, J. L. Science.,1990, 250, 1411. 10. Di Braccio, M.; Grossi, G.; Romoa, G.; Vargiu, L.; Mura, M.; Marongiu, M. E.; Eur. J. Med. Chem., 2001, 36, 935. 11. El-Sayed, A. M.; Khodairy, A.; Salah, H.; Abdel-Ghany, H.; Phosphorus Sulfur Silicon Relat. Elem., 2007, 182, 711. 12. Nagaraja, G. K.; Vaidya, V. P.; Rai, K. S.; Mahadevan, K. M.; Phosphorus Sulfur Silicon Relat. Elem., 2006, 181, 2797. 13. Nabih, K.; Baouid, A.; Hasnaoui, A.; Kenz, A.; Synth. Commun., 2004, 34, 3565. 14. Reddy, K. V. V.; Rao, P. S.; Ashok, D.; Synth. Commun., 2000, 30, 1825. 15. Haris, R. C.; Straley, J. M.U.S. Patent 1,537,757,1968; [Chem. Abstr., 1970, 73, 100054w]. 16. Claramunt, R. M.; Sanz, D.; Aggarwal, S.; Kumar, A.; Prakash, O.; Singh, S.P.; Elgueroc, J.; Arkivoc., 2006, 35. 17. Herbert, J. A. L.; Suschitzky, H.; J. Chem. Soc.; Perkin Trans.,1974, 1,2657. 18. Morales, H. R.; Ulbarela, B. A.; Contreras, R.; Heterocycles., 1986, 24, 135. 19. Jung, D. I.; Choi, T. W.; Kim, Y. Y.; Kim, I. S.; Park, Y. M.; Lee, Y. G.; Jung, D. H.; Synth. Commun., 1999, 29, 1941. 20. Balakrishna, M. S.; Kaboudin, B.; Tetrahedron Lett., 2001, 42, 1127. 21. Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O.; Tetrahedron Lett., 2001, 42, 3193. 22. Kaboudin, B.; Navaee, K.; Heterocycles, 2001, 55, 1443. 23. Pozarentzi, M.; Stephanatou, J. S.; Tsoleridis, C. A.; Tetrahedron Lett., 2002, 43, 1755. 24. Yadav, J. S.; Reddy, B. V. S.; Eshwaraiah, B.; Anuradha, K.; Green Chem., 2002, 4,592. 25. Jarikote, D. V.; Siddiqui, S. A.; Rajagopal, R.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V.; Tetrahedron Lett., 2003, 44, 1835. Department of Chemistry, <strong>Saurashtra</strong> <strong>University</strong>, Rajkot-360005 231
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