Novel complex n-heterocycles via intramolecular 1,5-electrocyclizations: l,2,4,4a,5,5a,10-octahydropyrido[4",3":2',3']cyclobuta[1',2':4,5] pyrrolo[2,3-b]pyridines

Heterocycles

Volumn 48, Issue 8, 1998, Pages 1581-1591

  Walter, Harald ^a   Sundermann, Garsten ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 18844363150     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-98-8190     Document Type: Article

References (16)

1. For a 'Progress Report'see: H. Walter, J. Prakt. Chem., 1998, 340, 309.
2. H. Walter, Ciba-Geigy-AG, German Patent 4,115,535
3. (Chem. Abstr., 1991, 116, 108299g).
4. H. Walter, H. Sauter, and T. Winkler, Helv. Chim. Acta, 1992, 75, 1274.
5. H. Walter, Helv. Chim. Acta, 1994, 77, 608.
6. H. Walter, H. Sauter and J. Schneider, Helv. Chim. Acta, 1993, 76, 1469.
7. H. Walter and J. Schneider, Heterocycles, 1995, 41, 1251.
8. (a) H. R. Howard, Pfizer Inc., International Patent Application WO 92/12979,
9. (Chem. Abstr., 1992, 117, 234000m).
10. (b) M. E. Konshin and V. P. Chesnokov, Khim. Geterosikl. Soedin., 1973, 10, 1391.
11. For a more complete discussion of mechanistic details see references 5 and 6.
12. G. Bodenhausen and D. J. Ruben, J. Chem. Phys. Lett., 1980, 69, 185.
13. 1H-NMR spectra of the two benzoyl substituted compounds (11) and (12) gave clear evidence for the presence of rotamers ( possible rotation about the C-N amide bond). For a more detailed discussion on rotamers in the piperidine-series see: D. M. Lynch and N. Cole, J. Org. Chem., 1966, 31, 3337.
14. (a) A. Leborgne, M. Moreau, and N. Spassky, Tetrahedron Lett., 1983, 24, 1027.
15. (b) D. P. Reynolds, J. C. Hollerton, and A. Richards, Anal. Appl. Spectrosc., 1988, 346.
16. C. Benson, P. Cay, M. Colon, M. A. Haiza, M. Tokles, and J. K. Snyder, J. Org. Chem., 1988, 53, 5335.