Pd(0)-catalyzed intramolecular Heck reaction: a versatile route for the synthesis of dibenzoazocinone derivatives

Tetrahedron Letters

Volumn 50, Issue 34, 2009, Pages 4866-4869

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

^a UNIVERSITY OF KALYANI   (India)

Author keywords

8 Exo trig; Aza Claisen rearrangement; Benzoazocinone; Heck reaction; Palladium catalyst

Indexed keywords

AZOCINE DERIVATIVE; DIBENZOAZOCINONE DERIVATIVE; NITROGEN; PALLADIUM; PHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; HECK REACTION; ISOMERIZATION; SYNTHESIS;

EID: 67649836087     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.06.030     Document Type: Article

References (32)

1. For Beckmann rearrangement, see:. Danaruma L.G., and Heldt W.E. Org. React. 11 (1960) 1
2. For Schmidt rearrangement, see:. Wolff H. Org. React. (1946) 307
3. Kunick C. Arch. Pharm. (Weinheim) 324 (1991) 579
4. Cho H., Murakami K., Nakanishi H., Isoshima H., Hayakawa K., and Uchida I. Heterocycles 48 (1998) 919
5. Cho H., Murakami K., Nakanishi H., Fujisawa A., Isoshima H., Niwa M., Hayakawa K., Hase Y., Uchida I., Watanabe H., Wakitani K., and Aisaka K. J. Med. Chem. 47 (2004) 101
6. Cho H., Murakami K., Fujisawa A., Niwa M., Nakanishi H., and Uchida I. Heterocycles 48 (1998) 1555
7. Basavaiah D., and Aravindu K. Org. Lett. 9 (2007) 2453
8. Jozsef, R.; Ivan, B.; Csaba, K.; Imre, H.; Miklos, N. (Gyar, E. Gy. T. G.) German Offen. Patent 2 608 186, 1976; Chem. Abstr. 1976, 85, 192593v.
9. D'Amico, J. J. (Monsanto Co.) Br. Patent 1 167 084, 1967; Chem. Abstr. 1970, 72, 12603y.
10. Tadashi, O.; Tsuyosmi, K.; Hisao, Y. (Sumitomo Chemical Co., Ltd) Jpn. 75 01 276, 1975; Chem. Abstr. 1975, 83, 43213c.
11. Arnold, B.; Benjamin, P.; Sheldon, S. (Hoffmann-La Roche, F., and Co., A.-G.) German Offen. Patent 2 353 062, 1974, Chem. Abstr. 1974, 81, 37487n.
12. Casadio S., Pala G., Crescenzi E., Uberti E.M., Coppi G., and Turba C. J. Med. Chem. 11 (1968) 97
13. Fink B.E., Gavai A.V., Tokarski J.S., Goyal B., Misra R., Xiao H.-Y., Kimball S.D., Han W.-C., Norris D., Spires T.E., You D., Gottardis M.M., Lorenzi M.V., and Vite G.D. Bioorg. Med. Chem. Lett. 16 (2006) 1532
14. Klein J.E.M.N., Muller-Bunz H., Ortin Y., and Evans P. Tetrahedron Lett. 49 (2008) 7187
15. Rigby J.H., Hughes tR.C., and Heeg M.J. J. Am. Chem. Soc. 117 (1995) 7834
16. Jeffery T. J. Chem. Soc., Chem. Commun. (1984) 1287
17. Gibson S.E., and Middleton R. J. Chem. Commun. 52 (1995) 1743
18. Gibson S.E., Guillo N., Middleton R.J., Thuílliez A., and Tozer M.J. J. Chem. Soc., Perkin Trans. 1 (1997) 447
19. Yet L. Chem. Rev. 100 (2000) 2963
20. Majumdar K.C., Chattopadhyay B., and Taher A. Synthesis (2007) 3647
21. Majumdar K.C., Pal A.K., Taher A., and Debnath P. Synthesis (2007) 1701
22. Majumdar K.C., and Chattopadhyay B. Synlett (2008) 979
23. Majumdar K.C., Chattopadhyay B., and Pal A.K. Lett. Org. Chem. 5 (2008) 276
24. Majumdar K.C., Chattopadhyay B., and Chakravorty S. Synthesis (2009) 674
25. Majumdar K.C., Chattopadhyay B., and Samanta S. Tetrahedron Lett. 50 (2009) 3178
26. Jeffery T. Tetrahedron 52 (1996) 10113
27. Majumdar K.C., Chattopadhyay B., and Nath S. Tetrahedron Lett. 48 (2008) 1609
28. Tsuji J. Palladium Reagents and Catalysts. New Perspective for the 21st Century (2004), Wiley 2nd Chapter
29. Beletskaya I.P., and Cheprakov A.V. Chem. Rev. 100 (2000) 3009
30. Majumdar K.C., and Chattopadhyay B. Curr. Org. Chem. 13 (2009) 731
31. Leggy A.A., Wenchen L., and Guy R.K. Org. Lett. 6 (2004) 3005
32. Majumdar, K. C.; Chattopadhyay, B. Synthesis 2009. Available online June 2008.