Novel synthesis of medium-sized heterocycles by palladium-catalyzed intramolecular Heck reaction via 9-endo-trig mode of cyclization

Synthesis

Volumn , Issue 14, 2009, Pages 2385-2392

  Majumdar, K C ^a   Chattopadhyay, Buddhadeb ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

9 endo trig; Claisen rearrangement; Intramolecular Heck reaction; Nine membered ring; Palladium acetate

Indexed keywords

9-ENDO-TRIG; CLAISEN REARRANGEMENT; INTRAMOLECULAR HECK REACTION; NINE-MEMBERED RING; PALLADIUM ACETATE;

CYCLIZATION; ETHERS; PALLADIUM;

ORGANOMETALLICS;

HETEROCYCLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CLAISEN REARRANGEMENT; CYCLIZATION; HECK REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 67651092402     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217395     Document Type: Article

References (32)

1. (a) Horwell, D. C.; Nichols, P. D.; Ratcliffe, G. S.; Roberts, E. J. Org. Chem. 1994, 59, 4418.
2. (b) Gibson (nee Thomas), S. E.; Jones, J. O.; McCague, R.; Tozer, M. J.; Whitcombe, N. J. Synlett 1999, 954.
3. (c) Kalinin, A. V.; Chauder, B. A.; Rakhit, S.; Snieckus, V. Org. Lett. 2003, 5, 3519.
4. (a) Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.
5. (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881.
6. (c) Yet, L. Chem. Rev. 2000, 100, 2963.
7. Carl, K. L. US Patent 4 073 912, 1972; Chem. Abstr. 1978, 89, 24156.
8. D'Amico, J. J. Monsanto Co., British Patent 1 167 084, 1967; Chem. Abstr. 1970, 72, 12603y.
9. Arnold, B.; Benjamin, P.; Sheldon, S. (Hoffmann-La Roche F. and Co. AG) German Patent 2 353 062, 1974; Chem. Abstr. 1974, 81, 3748n.
10. (a) Majumdar, K. C.; Chattopadhyay, B.; Ray, K. Tetrahedron Lett. 2007, 48, 7633.
11. (b) Majumdar, K. C.; Chattopadhyay, B.; Sinha, B. Tetrahedron Lett. 2008, 49, 1319.
12. (a) Linde, H. H. A. Helv. Chim. Acta 1965, 48, 1822.
13. (b) Abraham, D. J.; Rosenstein, R. D.; Lyon, R. L.; Fong, H. H. S. Tetrahedron Lett. 1972, 13, 909.
14. Kam, T.-S.; Tee, Y.-M.; Subramaniam, G. Nat. Prod. Lett. 1988, 12, 307.
15. Baudoin, O.; Guenard, D.; Gueritte, F. Mini-Rev. Org. Chem. 2004, 1, 333.
16. (a) Majumdar, K. C.; Chattopadhyay, B.; Taher, A. Synthesis 2007, 3647.
17. (b) Majumdar, K. C.; Pal, A. K.; Taher, A.; Debnath, P. Synthesis 2007, 1701.
18. (c) Majumdar, K. C.; Chattopadhyay, B. Synlett 2008, 979.
19. (d) Majumdar, K. C.; Chattopadhyay, B.; Nath, S. Tetrahedron Lett. 2008, 49, 1609.
20. (e) Majumdar, K. C.; Chattopadhyay, B.; Pal, A. K. Lett. Org. Chem. 2008, 5, 276.
21. (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
22. (b) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
23. (c) Milne, J. E.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 13028.
24. (a) Christoph, G.; Buchwald, S. L. Chem. Eur. J. 1999, 5, 3107.
25. (b) Bumagin, N. A.; Bykov, V. V.; Sukhomlinova, L. I.; Tolstaya, T. P.; Beletskaya, I. P. J. Organomet. Chem. 1995, 486, 259.
26. (c) Bumagin, N. A.; More, P. G.; Beletskaya, I. P. J. Organomet. Chem. 1989, 371, 397.
27. Arnold, L. A.; Luo, W.; Guy, R. K. Org. Lett. 2004, 6, 3005.
28. Otter, B. A.; Taube, A.; Fox, J. J. J. Org. Chem. 1971, 36, 1251.
29. (a) Gazith, M.; Noys, R. M. J. Am. Chem. Soc. 1955, 77, 6091.
30. (b) Gardner, I. J.; Noys, R. M. J. Am. Chem. Soc. 1961, 83, 2409.
31. Majumdar, K. C.; Khan, A. T. Synth. Commun. 1987, 17, 1589.
32. Gibson, S. E.; Guillo, N.; Middleton, R. J.; Thuilliez, A.; Tozer, M. J. J. Chem. Soc., Perkin Trans. 1 1997, 447.