Tributyltin hydride-mediated cyclisations of cinnamic enamides to piperidin-2-ones or pyrrolidin-2-ones. Indolizidinone ring formation by tandem radical cyclisation

Tetrahedron

Volumn 60, Issue 37, 2004, Pages 8181-8188

  Flisińska Łuczak, Joanna ^a   Leśniak, Stanisław ^a   Nazarski, Ryszard B ^a  

^a UNIVERSITY OF LODZ   (Poland)

Author keywords

Enamides; Indolizine; Lactams; Tandem radical cyclisation; Tributyltin hydride

Indexed keywords

AMIDE; FREE RADICAL; KETONE DERIVATIVE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; TIN DERIVATIVE; TOLUENE; TRIBUTYLTIN;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CYCLIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; THERMODYNAMICS;

EID: 4143050392     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.095     Document Type: Article

References (34)

1. Bowman, W. R.; Fletcher, A. J.; Potts, G. B. S. J. Chem. Soc., Perkin Trans. 1 2002, 2747-2762, and references cited therein.
2. E.J. Enholm, and G. Prasad Tetrahedron Lett. 30 1989 4939 4942
3. E.J. Enholm, and K.S. Kinter J. Am. Chem. Soc. 113 1991 7784 7785
4. E.J. Enholm, and K.S. Kinter J. Org. Chem. 60 1995 4850 4855
5. E.J. Enholm, and J.A. Buroff Tetrahedron 53 1997 13583 13602
6. A.F. Parsons, and R.M. Pettifer Tetrahedron Lett. 38 1997 5907 5910
7. A.F. Parsons, and R.M. Pettifer J. Chem. Soc., Perkin Trans. 1 1998 651 660
8. D. Bebbington, J. Bentley, P.A. Nilsson, and A.F. Parsons Tetrahedron Lett. 41 2000 8941 8945
9. J. Bentley, P.A. Nilsson, and A.F. Parsons J. Chem. Soc., Perkin Trans. 1 2002 1461 1469
10. S. Leśniak, and J. Flisińska Synthesis 2001 135 139
11. A.F. Parsons, and D.A.J. Williams Tetrahedron 54 1998 13405 13420
12. Nazarski, R. B.; Leśniak, S. In preparation.
13. C.A.G. Haasnoot, F.A.A.M. de Leeuw, and C. Altona Tetrahedron 36 1980 2783 2792
14. Granovsky, A. A. PC GAMESS, ver. 6.2, September 2001, http://classic.chem.msu.su/gran/gamess/index.html (b). GAMESS, Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347-1363.
15. Granovsky, A. A. PC GAMESS, ver. 6.2, September 2001, http://classic.chem.msu.su/gran/gamess/index.html (b). GAMESS, Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347-1363.
16. Preliminary results: Nazarski, R. B.; Leśniak, S. Abstracts. 36th Polish Seminar on the Nuclear Magnetic Resonance and Its Applications, Kraków, December 3-4, 2001, poster P10; Report INP No 1885/AP, p 51.
17. Leśniak, S.; Pasternak, B., in preparation.
18. S.R. Baker, A.F. Parsons, J.-F. Pons, and M. Wilson Tetrahedron Lett. 39 1998 7197 7200
19. S.R. Baker, K.I. Burton, A.F. Parsons, J.-F. Pons, and M. Wilson J. Chem. Soc., Perkin Trans. 1 1999 427 436
20. T. Sato, N. Nakamura, K. Ikeda, M. Okada, H. Ishibashi, and M. Ikeda J. Chem. Soc., Perkin Trans. 1 1992 2399 2407
21. D.C. Spellmeyer, and K.N. Houk J. Org. Chem. 52 1987 959 974
22. (a) Wolinski, K.; Hilton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260, and references cited therein.
23. (b) Rauhut, G.; Puyear, S.; Wolinski, K.; Pulay, P. J. Phys. Chem. 1996, 100, 6310-6316.
24. (c) Cheeseman, J. R.; Trucks, G. W.; Keith, T. A.; Frisch, M. J. J. Chem. Phys. 1996, 104, 5497-509.
25. (d) Forsyth, D. A.; Sebag, A. B. J. Am. Chem. Soc. 1997, 119, 9483-94.
26. (e) Wiberg, K. B. J. Comput. Chem. 1999, 20, 1299-1303.
27. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.6; Gaussian, Inc.: Carnegie Office Park, Bldg. 6, Pittsburgh, PA 15106, USA, 1998.
28. A.M. Rosa, A.M. Lobo, P.S. Branco, S. Prabhakar, and A.M.D.L. Pereira Tetrahedron 53 1997 269 284
29. F. Aldabbagh, W.R. Bowman, and E. Mann Tetrahedron Lett. 38 1997 7937 7940
30. F. Aldabbagh, W.R. Bowman, E. Mann, and A.M.Z. Slawin Tetrahedron 55 1999 8111 8128
31. W.R. Bowman, E. Mann, and J. Parr J. Chem. Soc., Perkin Trans. 1 2000 2991 2999
32. A. Cobas, E. Guitian, and L. Castedo J. Org. Chem. 58 1993 3113 3117
33. G. Wolf, and E.U. Wuerthwein Chem. Ber. 124 1991 655 663
34. J.O. Madsen, M. Meldal, S. Mortensen, and B. Olsson Acta Chem. Scand. Ser. B 35 1981 77 82