Palladium(0)-catalyzed intramolecular heck reaction: A resourceful route for the synthesis of naphthoxepine naphthoxocine derivatives

Synthesis

Volumn , Issue 21, 2009, Pages 3593-3602

  Majumdar, K C ^a   Ansary, Inul ^a   Sinha, Biswajit ^a   Chattopadhyay, Buddhadeb ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

Catalysis; Heck cyclization; Oxepines; Oxocines; Palladium; Wittig olefination

Indexed keywords

HECK CYCLIZATION; HECK REACTIONS; OXOCINES; WITTIG OLEFINATION;

CATALYSIS; PALLADIUM;

CYCLIZATION;

AMINE; NAPHTHOXEPINE; OXEPINE DERIVATIVE; OXOCINE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; HECK REACTION; OLEFINATION; OXIDATION; OZONOLYSIS;

EID: 72049085033     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/S-0029-1216984     Document Type: Article

References (54)

1. (a) Devon, T. K.; Scott, A. I. Hand Book of Naturally Occurring Compounds, Vol.II; Academic: New York, NY, 1972.
2. (b) Faulkner, D. J. Nat. Prod 1989, 5, 613.
3. Carl, K.; Joseph, L. US Patent 4073912, 1972;
4. Chem. Abstr. 1978, 89, 24156.
5. (a) Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981,14, 95.
6. (b) Yet, L. Chem. Rev. 2000,100, 2963.
7. (c) Hoberg, J. O. Tetrahedron 1998, 54, 12631.
8. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, NY, 1994.
9. For a review on medium-ring nitrogen heterocycles, see: Evans, P. A.; Holmes, A. B. Tetrahedron 1991, 47, 9191.
10. For reviews, see: (a) Dieters, A.; Martin, S. F. Chem. Rev. 2004,104, 2199.
11. (b) Schmidt, B. Eur. J. Org. Chem. 2004, 1865.
12. (c)Trnka, T.M.;Grubbs, R.H. Acc. Chem. Res. 2001, 34, 18.
13. (d) Furstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012.
14. (e) Maier, M. E. Angew. Chem. Int. Ed. 2000, 39, 2073.
15. (f) Blechert, S. Pure Appl. Chem. 1999, 71, 1393.
16. (g) Schrock, R. R. Tetrahedron 1999, 55, 8141.
17. (h) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
18. (i) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
19. (j) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036.
20. (k) Schmalz, H. G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833.
21. (l) Kotha, S.; Sreenivasachary, N. Indian J. Chem., Sect. B: Org. Chem. Incld. Med. Chem. 2001, 40, 763.
22. (m) Ghosh, S.; Ghosh, S.; Sarkar, N. J. Chem. Sci. 2006, 118, 223.
23. (a) TenBrink, R. E.; McCall, J. M.; Johnson, H. G. J. Med. Chem. 1980, 23, 1058.
24. (b) TenBrink, R. E.; McCall, J. M.; Pals, D. T.; McCall, R. B.; Orley, J.; Humphrey, S. J.; Wendling, M. G. J. Med. Chem. 1981, 24, 64.
25. (c) O'Shea, D. F.; Sharp, J. T. J. Chem. Soc., Perkin Trans. 1 1995, 515.
26. (a) Tretter J. R., US Patent 3514449, 1970;
27. Chem. Abstr. 1970, 73, 35404u.
28. (b) Dictionary of Drugs, 1st ed.; Elks, J.; Ganellin, C. R., Eds.; Chapman and Hall: London, 1990, 984.
29. Stefinovic, M.; Snieckus, V. J. Org. Chem. 1998, 63, 2808.
30. (a) Kishuku, H.; Shindo, M.; Shishido, K. Chem. Commun. 2003, 350.
31. (b) Sabui, S. K.; Venkateswaran, R. V. Tetrahedron Lett. 2004, 45, 983.
32. (c) Lecornue, F.; Ollivier, J. Synlett 2004, 1613.
33. (d) Vyvyan, J. R.; Oaksmith, J. M.; Parks, B. W.; Peterson, E. M. Tetrahedron Lett. 2005, 46, 2457.
34. Satoh, Y.; Libby, A. H.; Powers, C.; Kowalski, T.; White, D. H.; Kimble, E. F. Bioorg. Med. Chem. Lett. 1994, 4, 549.
35. Kiyama, R.; Honma, T.; Hayashi, K.; Ogawa, M.; Hara, M.; Fujimoto, M.; Fujishita, T. J. Med. Chem. 1995, 38, 2728.
36. Majumdar, K. C.; Chattopadhyay, B.; Sinha, B. Tetrahedron Lett. 2008, 49, 1319.
37. (a) Majumdar, K. C.; Islam, R.; Rahaman, H.; Roy, B. Org. Biomol. Chem. 2006, 4, 2393.
38. (b) Majumdar, K. C.; Maji, P. K.; Ray, K.; Debnath, P. Tetrahedron Lett. 2007, 48, 9127.
39. (c) Majumdar, K. C.; Ray, K.; Debnath, P.; Maji, P. K.; Kundu, N. Tetrahedron Lett. 2008, 49, 5597.
40. (d) Majumdar, K. C.; Taher, A. Tetrahedron Lett. 2009, 50, 228.
41. (e) Majumdar, K. C.; Debnath, P.; Samanta, S. Lett. Org. Chem. 2007, 4, 309.
42. (a) Majumdar, K. C.; Chattopadhyay, B.; Ray, K. Tetrahedron Lett. 2007,48, 7633.
43. (b) Majumdar, K. C.; Chattopadhyay, B. Synlett 2008, 979.
44. (c) Majumdar, K. C.; Mondai, S. Synlett 2008, 2851.
45. (d) Majumdar, K. C.; Chattopadhyay, B.; Taher, A. Synthesis 2007, 3647.
46. (e) Majumdar, K. C.; Chakravorty, S.; Shyam, P. K.; Taher, A. Synthesis 2009, 403.
47. (f) Majumdar, K. C.; Sinha, B.; Maji, P. K.; Chattopadhyay, S. K. Tetrahedron 2009, 65, 2751.
48. (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
49. (b) Gibson, S. E.; Guillo, N.; Middleton, R. J.; Thuilliez, A.; Tozer, M. J. J. Chem. Soc., Perkin Trans. 1 1997, 447.
50. Arnold, L. A.; Luo, W.; Guy, R. K. Org. Lett. 2004, 6, 3005.
51. (a) Gazith, M.; Noys, R. M. J. Am. Chem. Soc. 1955, 77, 6091.
52. (b) Gardner, I. J.; Noys, R. M. J. Am. Chem. Soc. 1961, 83, 2409.
53. Jeffery, T. Tetrahedron 1996, 52, 10113.
54. Majumdar, K. C.; Chattopadhyay, B.; Sinha, B. Synthesis 2008, 3857.