Synthesis of N-protected cyano aziridines

Synlett

Volumn , Issue 6, 2004, Pages 1083-1085

  Fioravanti, Stefania ^a   Morreale, Alberto ^a   Pellacani, Lucio ^a   Tardella, Paolo A ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Aminations; Carbamates; Michael additions; Nitriles; Ring closure

Indexed keywords

AZIRIDINE DERIVATIVE; CALCIUM OXIDE; CARBAMIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; NITRILE;

AMINATION; ARTICLE; CHEMICAL REACTION KINETICS; DRUG STRUCTURE; DRUG SYNTHESIS; MICHAEL ADDITION; STEREOCHEMISTRY;

EID: 3142736344     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-820047     Document Type: Article

References (32)

1. (a) Bicker, U. W. In Immune Modulation Agents and their Mechanisms; Fenical, R. G.; Chirigos, M. A., Eds.; Marcel Dekker: New York and Basel, 1984, 447.
2. (b) Iyengar, B. S.; Dorr, R. T.; Alberts, D. S.; Hersh, E. M.; Salmon, S. E.; Remers, W. A. J. Med. Chem. 1999, 42, 510.
3. Iyengar, B. S.; Dorr, R. T.; Remers, W. A. J. Med. Chem. 2004, 47, 218.
4. (a) Remers, W.; Iyengar, B. US 6476236, 2002; Chem. Abstr. 2002, 137, 337772.
5. (b) Lopez-Berestein, G.; Remers, W. A.; Hersh, E. M. PCT Int. Appl. 2002041871, 2002; Chem. Abstr. 2002, 137, 10970.
6. (c) Kitagawa, S.; Minafuji, M.; Yokoi, T. Jpn. Kokai Tokkyo Koho JP 61140561, 1986; Chem. Abstr. 1987, 106, 50009.
7. (d) Bosies, E.; Berger, H.; Kampe, W.; Bicker, U.; Grafe, A. US 4410532, 1983; Chem. Abstr. 1984, 100, 68151.
8. (e) Berger, H.; Gall, R.; Kampe, W.; Bicker, U.; Kuhn, R. Ger. Offen DE 2948832, 1981; Chem. Abstr. 1981, 95, 115257.
9. Boukhris, S.; Souizi, A. Tetrahedron Lett. 2003, 44, 3259.
10. (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
11. (b) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341.
12. (c) Stamm, H. J. Prakt. Chem. 1999, 4, 319.
13. (d) Atkinson, R. S. Tetrahedron 1999, 55, 1519.
14. (e) McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
15. (f) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247.
16. (a) Goodridge, T. H.; Huntress, W. T.; Bratzell, R. P. Cancer Chemother. Rep. 1963, 26, 341.
17. (b) Dermer, O. C.; Ham, G. E. Ethyleneimine and other Aziridines; Academic Press: New York and London, 1969, 425.
18. (a) Dauban, P.; Dodd, R. H. Tetrahedron Lett. 1998, 39, 5739.
19. (b) Schirmeister, T.; Peric, M. Bioorg. Med. Chem. 2000, 8, 1281.
20. (a) Fioravanti, S.; Morreale, A.; Pellacani, L.; Tardella, P. A. Synthesis 2001, 1975.
21. (b) Fioravanti, S.; Morreale, A.; Pellacani, L.; Tardella, P. A. J. Org. Chem. 2002, 67, 4972.
22. (c) Colantoni, D.; Fioravanti, S.; Pellacani, L.; Tardella, P. A. Org. Lett. 2004, 6, 197.
23. Texier-Boullet, F.; Foucaud, A. Tetrahedron Lett. 1982, 23, 4927.
24. Lwowski, W.; Maricich, T. J. J. Am. Chem. Soc. 1965, 87, 3630.
25. +: 194.0930; found: 194.0927.
26. Lwowski, W. In Nitrenes; Lwowski, W., Ed.; John Wiley and Sons: New York, 1970, Chap. 6.
27. Fioravanti, S.; Morreale, A.; Pellacani, L.; Tardella, P. A. Eur. J. Org. Chem. 2003, 4549.
28. (a) Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Hodgson, P. K. G.; Langridge-Smith, P. R. R.; Millar, J. R. A.; Taylor, A. T. J. Chem. Soc., Chem. Commun. 1995, 885.
29. 13 and: Fioravanti, S.; Marchetti, F.; Morreale, A.; Pellacani, L.; Tardella, P. A. Org. Lett. 2003, 5, 1019.
30. 10
31. (a) De Kimpe, N.; Sulmon, P.; Verhé, R.; De Buyck, L.; Schamp, N. J. Org. Chem. 1983, 48, 4320.
32. (b) Charrier, J.; Foucaud, A.; Person, H.; Loukakou, E. J. Org. Chem. 1983, 48, 481.