Synthesis of highly substituted dibenzoazocine derivatives by the aza-Claisen rearrangement and intramolecular Heck reaction via 8-exo-trig mode of cyclization

Tetrahedron Letters

Volumn 50, Issue 26, 2009, Pages 3178-3181

  Majumdar, K C ^a   Chattopadhyay, Buddhadeb ^a   Samanta, Srikanta ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

8 Exo trig; Aza Claisen rearrangement; Dibenzoazocine; Heck reaction

Indexed keywords

AZOCINE DERIVATIVE; DIBENZOAZOCINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 65549129214     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.01.105     Document Type: Article

References (51)

1. Bertha C.M., Ellis M., Filippen-Anderson J.L., Porreca F., Rothman R.B., Davis P., Xu H., Becktts K., and Rice K.C. J. Med. Chem. 38 (1996) 2081
2. Alvarez M., and Joule A. Alkaloids; Chemistry and Biology Vol. 57 (2001), Academic Press, New York
3. Kessel B.J., and Simpson M.G. In: Kaplan H.I., and Sadock B.J. (Eds). Comprehensive Textbook of Psychiatry Vol. 2 (1995), Williams and Wilkins, Baltimore 2095
4. Gil L., Gil R.P.d.F., dos Santos D.C., and Marazano C. Tetrahedron Lett. 41 (2000) 6067
5. Gulias M., Garcia R., Delgado A., Castedo L., and Mascarenas J.L. J. Am. Chem. Soc. 128 (2006) 384
6. Bandini M., Melloni A., Piccinelli F., Sinisi R., Tommasi S., and Bonchi A.U. J. Am. Chem. Soc. 128 (2006) 1424
7. Yip K.T., Yang M., Law K.L., Zhu N.Y., and Yang D. J. Am. Chem. Soc. 128 (2006) 3130
8. Kamijo S., and Yamamoto Y. Angew. Chem., Int. Ed. 41 (2002) 3230
9. Wtulski B., Alayrac C., and Saeftel L. Angew. Chem., Int. Ed. 42 (2003) 4257
10. Majumdar K.C., and Chattopadhyay B. Synlett (2008) 979
11. Majumdar K.C., Chattopadhyay B., and Ray K. Tetrahedron Lett. 48 (2007) 7633
12. Majumdar K.C., Chattopadhyay B., and Sinha B. Tetrahedron Lett. 49 (2008) 1319
13. Majumdar K.C., Sinha B., Chattopadhyay B., and Ray K. Tetrahedron Lett. 49 (2008) 4405
14. Majumdar K.C., Chattopadhyay B., and Sinha B. Synthesis (2008) 3857
15. Majumdar K.C., Chattopadhyay B., and Chakravorty S. Synthesis (2009) 674
16. Majumdar K.C., Mondal S., and De N. Synlett (2008) 2851
17. Gibson S.E., Guillo N., Jones J.O., Buck I.M., Kalindjian S.B., Roberts S., and Tozer M.J. Eur. J. Med. Chem. 37 (2002) 379
18. Gibson S.E., Guillo N., Middleton R.J., Thuilliez A., and Tozer M.J. J. Chem. Soc., Perkin Trans. 1 (1997) 447
19. Gibson S.E., and Middleton R.J. J. Chem. Soc., Chem. Commun. (1995) 1743
20. Gibson S.E., Jones J.O., McCague R., Tozer M.J., and Whitcombe N.J. Synlett (1999) 954
21. Gibson S.E., Guillo N., Kalindjian S.B., and Tozer M.J. Bioorg. Med. Chem. Lett. 7 (1997) 1289
22. Gibson S.E., Mainolfi N., Kalindjian S.B., and Wright P.T. Chem. Commun. (2003) 1568
23. Arnold L.A., and Guy R.K. Bioorg. Med. Chem. Lett. 16 (2006) 5360
24. Alcaide B., Almendros P., and Rodriguez-Acebes R. J. Org. Chem. 70 (2005) 2713
25. Molander G.A., and Dehmel F. J. Am. Chem. Soc. 126 (2004) 10313
26. Park C.-H., Ryabova V., Seregin I.V., Sromek A.W., and Gevorgyan V. Org. Lett. 6 (2004) 1159
27. David E., Perrin J., Pellet-Rostaing S., Chabert J.F., and Lemaire M. J. Org. Chem. 70 (2005) 3569
28. Glover B., Harvey K.A., Liu B., Sharp M.J., and Tymoschenko M.F. Org. Lett. 5 (2003) 301
29. Sezen B., and Sames D. J. Am. Chem. Soc. 125 (2003) 5274
30. Sezen B., and Sames D. J. Am. Chem. Soc. 125 (2003) 10580
31. Sezen B., and Sames D. Org. Lett. 5 (2003) 3607
32. Rieth R.D., Mankad N.P., Calimano E., and Sadighi J.P. Org. Lett. 6 (2004) 3981
33. Okazawa T., Satoh T., Miura M., and Nomura M. J. Am. Chem. Soc. 124 (2002) 5286
34. Yokooji A., Okazawa T., Satoh T., Miura M., and Nomura M. Tetrahedron 59 (2003) 5685
35. Kalyani D., Deprez N.R., Desai L.V., and Sanford M.S. J. Am. Chem. Soc. 127 (2005) 7330
36. For a review:. Zificsak C.A., and Hlasta D.J. Tetrahedron 60 (2004) 8991
37. Arnold L.A., Luo W., and Guy R.K. Org. Lett. 6 (2004) 3005
38. For some recent reviews on Claisen rearrangement, see:. Majumdar K.C., Alam S., and Chattopadhyay B. Tetrahedron 64 (2008) 597
39. Castro A.M. Chem. Rev. 104 (2004) 2939
40. Nubbemeyer U. Synthesis (2003) 961
41. Roe J.M., Webster R.A.B., and Ganesan A. Org. Lett. 5 (2003) 2825
42. Nubbemeyer U. Top. Curr. Chem. 244 (2005) 149
43. Correa A., Tellitu I., Dominguez E., and Sanmartin R. J. Org. Chem. 71 (2006) 8316
44. Gazith M., and Noys R.M. J. Am. Chem. Soc. 77 (1955) 6091
45. Gardner I.J., and Noys R.M. J. Am. Chem. Soc. 83 (1961) 2409
46. Majumdar K.C., Chattopadhyay B., and Nath S. Tetrahedron Lett. 49 (2008) 1609
47. Tsuji J. Palladium Reagents and Catalysts. New Perspective for the 21st Century (2004), Wiley 2nd Chapter
48. Illuminati G., and Mandolini L. Acc. Chem. Res. 14 (1981) 95
49. Beletskaya I.P., and Cheprakov A.V. Chem. Rev. 100 (2000) 3009
50. 2S: C, 61.28; H, 5.14; N, 2.98. Found: C, 61.58; H, 4.89; N, 3.11.
51. 2S: C, 74.00; H, 5.95; N, 3.60. Found: C, 74.19; H, 5.77; N, 3.71.