Structural and spatial considerations in the N,N′-diacyl- and bis(alkoxycarbonyl)bispidinone series

Journal of Organic Chemistry

Volumn 73, Issue 19, 2008, Pages 7793-7796

  Levinger, Shlomo ^a   Sharabi Ronen, Yifat ^a   Mainfeld, Alexander ^a   Albeck, Amnon ^a  

^a BAR ILAN UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; CHEMICAL REACTIONS;

CHEMICAL EQUATIONS; PLANAR CHIRALITY; SOLVENT POLARITY;

STEREOCHEMISTRY;

1,5 DIPHENYL 3,7 BIS[(2 PROPENYLOXY)CARBONYL] 3,7 DIAZABICYCLO[3.3.1]NONAN 9 ONE; 5,7 BIS(PHENYLMETHYL) 1,3 DIAZATRICYCLO[3.3.1.1 3,7]DECAN 6 ONE; AMIDE; CARBONYL DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; DRUG STRUCTURE; ISOMERISM; ISOMERIZATION;

AMIDES; CARBAMATES; PYRONES; SOLVENTS; STEREOISOMERISM;

EID: 53049092818     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801423a     Document Type: Article

References (38)

1. Arutyunyan, G. L.; Chachoyan, A. A.; Shkulev, V. A.; Adamyan, G. G.; Agadzhanyan, T. E.; Garibdzhanyan, B. T. Khim.-Farm. Zh. 1995, 29, 33-35;
2. Chem. Abstr. 124:117427.
3. Garrison, G. L.; Berlin, K. D.; Scherlag, B. J.; Lazzara, R.; Patterson, E.; Fazekas, T.; Sangiah, S.; Chen, C.-L.; Schubot, F. D.; van der Helm, D. J. Med. Chem. 1996, 39, 2559-2570.
4. Ruenitz, P. C.; Mokler, C. M. J. Med. Chem. 1977, 20, 1668-1671.
5. Smith, G. S.; Thompson, M. D.; Berlin, K. D.; Holt, E. M.; Scherlag, B. J.; Patterson, E.; Lazzara, R. Eur. J. Med. Chem. 1990, 25, 1-8.
6. Holzgrabe, U.; Brandt, W. J. Med. Chem. 2003, 46, 1383-1389.
7. Kuhl, U.; von Korff, M.; Baumann, K.; Burschka, C.; Holzgrabe, U. J. Chem. Soc., Perkin Trans. 2 2001, 2037-2042.
8. Wang, Y.; Tang, K.; Inan, S.; Siebert, D.; Holzgrabe, U.; Lee, D. Y. W.; Huang, P.; Li, J.-G.; Cowan, A.; Liu-Chen, L.-Y J. Pharmacol. Exp. Ther. 2005, 312, 220-230;
9. Chem. Abstr. 142:329635.
10. Michael, J. P. Nat. Prod. Rep. 1997, 14, 21-41.
11. Black, D. S. C.; Deacon, G. B.; Rose, M. Tetrahedron 1995, 51, 2055-2076.
12. Comba, P.; Kanellakopulos, B.; Katsichtis, C.; Lienke, A.; Pritzkow, H.; Rominger, F. J. Chem. Soc., Dalton Trans. 1998, 3997-4002.
13. Comba, P.; Nuber, B.; Ramlow, A. J. Chem. Soc., Dalton Trans. 1997, 347-352.
14. Hancock, R. D.; Pattrick, G.; Wade, P. W.; Hosken, G. D. Pure Appl. Chem. 1993, 65, 473-476.
15. Hosken, G. D.; Allan, C. C.; Boeyens, J. C. A.; Hancock, R. D. J. Chem. Soc. Dalton Trans. 1995, 3705-3708.
16. Vrancken, E.; Alexakis, A.; Mangeney, P. Eur. J. Org. Chem. 2005, 1354-1366.
17. Kocienski, P. J.; Christopher, J. A.; Bell, R.; Otto, B. Synthesis 2005, 75-84.
18. Allen, B. D.; Cintrat, J.-C.; Faucher, N.; Berthault, P.; Rousseau, B.; O'Leary, D. J. J. Am. Chem. Soc. 2005, 127, 412-420.
19. Nuzillard, J.-M.; Connolly, J. D.; Delaude, C.; Richard, B.; Zeches-Hanrot, M.; Le Men-Olivier, L. Tetrahedron 1999, 55, 11511-11518.
20. Yamawaki, I.; Bukovac, S. W.; Sunami, A. Chem. Pharm. Bull. 1994, 42, 2365-2369.
21. Brandt, W.; Drosihn, S.; Haurand, M.; Holzgrabe, U.; Nachtsheim, C. Arch. Pharm. (Weinheim. Ger.) 1996, 329, 311-323.
22. Arutyunyan, G. L.; Chachoyan, A. A.; Agadzhanyan, T. E.; Garibdzhanyan, B. T. Pharm. Chem. J. (Engl. Transl.) 1996, 30, 739-741;
23. Chem. Abstr. 127:29297.
24. Kuznetsov, A. I.; Basargin, E. B.; Moskovkin, A. S.; Ba, M. K.; Miroshnichenko, I. V.; Botnikov, M. Y.; Unkovskii, B. V. Khim. Geterotsikl. Soedin. 1985, 1679-1685;
25. Chem. Abstr. 105:42136.
26. Chiavarelli, S.; Settimj, G. Gazz. Chim. Ital 1958, 88, 1234-1245;
27. Chem. Abstr. 53:122272.
28. Stetter, H.; Schafer, J.; Dieminger, K. Chem. Ber. 1958, 91, 598-604.
29. McCabe, P. H.; Milne, N. J.; Sim, G. A. J. Chem. Soc., Chem. Commun. 1985, 625-626.
30. 32.
31. (b) Values taken from CRC Handbook of Chemistry and Physics, 72nd ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, 1991-1992; pp 849; 9-27.
32. Ôki, M. Applications of Dynamic NMR Spectroscopy to Organic Chemistry; VCH: Deerfield Beach, Florida, 1985; pp 334-335.
33. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley; New York, 1994; p 1166.
34. Schloegl, K. Top. Stereochem. 1967, 1, 39-91.
35. Schloegl, K. Pure Appl. Chem. 1970, 23, 413-432.
36. Donohoe, T. J.; Harji, R. R.; Moore, P. R.; Waring, M. J. J. Chem. Soc., Perkin Trans. 1 1998, 819-834.
37. Cahn, R. S.; Ingold, C.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1966, 5, 385-415.
38. IUPAC Compendium of Chemical Terminology; electronic version: http:// goldbook.iupac.org/R05273.html.