Palladium-mediated reductive Heck cyclization for the formation of dibenzoazepinone framework

Synlett

Volumn , Issue 19, 2009, Pages 3127-3130

  Majumdar, K C ^a   Chakravorty, Santanu ^a   Ghosh, Tapas ^a   Sridhar, B ^b  

^a UNIVERSITY OF KALYANI   (India)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Dibenzoazepinone; Pd(PPh 3)4; Reductive Heck; Sonogashira cross coupling

Indexed keywords

DIBENZAZEPINE DERIVATIVE; DIBENZOAZEPINONE; LIGAND; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CYCLIZATION; HECK REACTION; SONOGASHIRA REACTION; SYNTHESIS;

EID: 72049092379     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/S-0029-1218298     Document Type: Article

References (31)

1. (a) Link, J. T. Org. React. (N. Y.) 2002, 60, 157.
2. (b) Dyker, G. In Handbook of Organopalladium Chemistry for Organic Synthesis, Vol.1; Negishi, E.-I.; de Meijere, A., Eds.; Wiley: New York, 2002.
3. (a) Liu, P.; Huang, L.; Lu, Y.; Dilmeghani, M.; Baum, J.; Xiang, T.; Adams, J.; Tasker, A.; Larsen, R.; Faul, M. M. Tetrahedron Lett. 2007, 48, 2307.
4. (b) Mangeney, P.; Pays, C. Tetrahedron Lett. 2003, 44, 5719.
5. (c) Higuchi, K.; Comins, D. L. Beilstein J. Org. Chem. 2007,3,1.
6. (d) Majumdar, K. C.; Sinha, B.; Maji, P. K.; Chattopadhyay, S. K. Tetrahedron 2009, 65, 2751.
7. (e) Majumdar, K. C.; Chakravorty, S.; De,N. Tetrahedron Lett. 2008,49, 3419.
8. (f) Majumdar, K. C.; Chakravorty, S.; Shyam, P. K.; Taher, A. Synthesis 2009, 403.
9. (g) Majumdar, K. C.; Chakravorty, S.; Ray, K. Synthesis 2008, 2991.
10. (h) Majumdar, K. C.; Sinha, B.; Chattopadhyay, B.; Ray, K. Tetrahedron Lett. 2008, 49, 4405.
11. (a) Di Fabio, R.; Micheli, F.; Baraldi, D.; Bertani, B.; Conti, N.; Dal Forno, G.; Feriani, A.; Donati, D.; Marcchioro, C.; Messeri, T.; Missio, A.; Pasquarello, A.; Pentassuglia, G.; Pizzi, D. A.; Provera, S.; Quaglia, A. M.; Sabbatini, F. M. Farmaco 2003, 58, 723.
12. (b) Hayashi, M.; Sai, H.; Horikawa, H. Heterocycles 1998, 48, 1331.
13. (c) Majumdar, K. C.; Chattopadhyay, B.; Ray, K. Tetrahedron Lett. 2007, 48, 7633.
14. (d) Majumdar, K. C.; Chattopadhyay, B.; Samanta, S. Tetrahedron Lett. 2009, in press.
15. (e) Cropper, E. L.; Andrew, J. P.; White, A. F.; Hii, K. K. J. Org. Chem. 2006, 71, 1732.
16. (a) Arnold, L. A.; Luo, W.; Guy, R. K. Org. Lett. 2004, 6, 3005.
17. (b) Gibson, S. E.; Jones, J. O.; Kalindjinan, S. B.; Knight, J. D.; Steed, J. W.; Tozer, M. J. Chem. Commun. 2002, 1938.
18. (c) Alcaide, B.; Polanco, C.; Sierra, M. A. Eur. J. Org. Chem. 1998, 2913.
19. (d) Gibson, S. E.; Middleton, R. J. J. Chem. Soc., Chem. Commun. 1995, 1743.
20. (e) Majumdar, K. C.; Chattopadhyay, B.; Sinha, B. Tetrahedron Lett. 2008, 49, 1319.
21. (f) Majumdar, K. C.; Chattopadhyay, B. Synlett 2008, 979.
22. (g) For a recent review on this topic, see: Majumdar, K. C.; Chattopadhyay, B. Curr. Org. Chem. 2009, in press.
23. For example, see: (a) Santos, L. S.; Pilli, R. A. Synthesis 2002, 87.
24. (b) Tietze, L. F.; Sommer, K. M.; Schneider, G.; Tapolzsanyi, P.; Wolfling, J.; Muller, P.; Noltemeyer, M.; Terlau, H. Synlett 2003, 1494.
25. Kaufmann, D.; Fünfschilling, P. C.; Beutler, U.; Hoehn, P.; Lohse, O.; Zaugg, W. Tetrahedron Lett. 2004, 45, 5275.
26. Fauq, A. H.; Simpson, K.; Maharvi, G. M.; Golde, T.; Das, P. Bioorg. Med. Chem. Lett. 2007,17, 6392.
27. Kling, A.; Backfisch, G.; Delzer, J.; Geneste, H.; Graef, C.; Holzenkamp, U.; Hornberger, W.; Lange, U. E. W.; Lauterbach, A.; Mack, H.; Seitz, W.; Subkowski, T. Bioorg. Med. Chem. Lett. 2002,12, 441.
28. CCDC 747690 contains supplementary crystallographic data for the structure 4f.
29. 3: C, 60.13; H, 3.49; N, 2.70. Found: C, 60.33; H, 3.29; N, 2.93.
30. 3: C, 79.37; H, 4.87; N, 3.56. Found: C, 79.58; H, 5.04; N, 3.75.
31. 2-Bromobenzoic acid can also be used to give the corresponding 2-bromo derivative 3 which also undergoes reductive Heck cyclization to afford 4f (yield 80%).