Azidation of β-carbonyl lactones and lactams

Tetrahedron Letters

Volumn 50, Issue 38, 2009, Pages 5379-5381

  Kashinath, Dhurke ^a   Budin, Ghyslain ^a   Baati, Rachid ^a   Meunier, Stéphane ^a   Wagner, Alain ^a  

^a Faculté de Pharmacie   (France)

Author keywords

Azidation; Dicarbonyl; Proline; TBD; TsN3

Indexed keywords

AZIDE; BETA OXOCARBOXYLIC ACID ESTER; CARBONYL DERIVATIVE; ESTER; HETEROCYCLIC COMPOUND; LACTAM; LACTONE; PROLINE; UNCLASSIFIED DRUG;

ARTICLE; AZIDATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEACYLATION; HALOGENATION; SYNTHESIS;

EID: 68049099172     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.07.039     Document Type: Article

References (36)

1. Bräse S., Gil C., Knepper K., and Zimmermann V. Angew. Chem., Int. Ed. 44 (2005) 5188-5240 and references cited therein
2. Sahasrabudhe K., Gracias V., Furness K., Smith B.T., Katz C.E., Reddy D.S., and Aubé J. J. Am. Chem. Soc. 125 (2003) 7914-7922
3. Kumagai N., Matsunaga S., and Shibasaki M. Angew. Chem., Int. Ed. 43 (2004) 478-482
4. Palacios F., de Retana A.M.C., de Marigorta E.M., Rodriguez M., and Pagalday J. Tetrahedron 59 (2003) 2617-2623
5. Langer P., Freifeld I., and Shojaei H. Chem. Commun. (2003) 3044-3045
6. Obika S., Andoh J.-i., Onoda M., Nakagawa O., Hiroto A., Sugimoto T., and Imanishi T. Tetrahedron Lett. 44 (2003) 5267-5270
7. Feldman A.K., Colasson B., Sharpless K.B., and Fokin V.V. J. Am. Chem. Soc. 127 (2005) 13444-13445
8. Eguchi S. ARKIVOC (2005) 98-119 and references cited therein
9. Gololobov Y.G., and Kasukhin L.F. Tetrahedron 48 (1992) 1353-1406
10. Holla B.S., Mahalinga M., Karthikeyan M.S., Poojary B., Akberali P.M., and Kumari N.S. Eur. J. Med. Chem. 40 (2005) 1173-1178
11. Bencivenni G., Lanza T., Leardini R., Minozzi M., Nanni D., Spagnolo P., and Zanardi G. J. Org. Chem. 73 (2008) 4721-4724
12. Dedola S., Nepogodiev S.A., and Field R.A. Org. Biomol. Chem. 5 (2007) 1006-1017
13. Binder W.H., and Kluger C. Curr. Org. Chem. 10 (2006) 1791-1815
14. Kolb H.C., Finn M.G., and Sharpless K.B. Angew. Chem., Int. Ed. 40 (2001) 2004-2021
15. Oguri H., and Schreiber S.L. Org. Lett. 7 (2005) 47-50
16. Mashiko T., Kumagai N., and Shibasaki M. Org. Lett. 10 (2008) 2725-2728
17. Terada M., Nakano M., and Ube H. J. Am. Chem. Soc. 128 (2006) 16044-116045
18. Yang D., Yan Y.-L., and Lui B. J. Org. Chem. 67 (2002) 7429-7431
19. Li H., Wang Y., Tang L., Wu F., Liu X., Guo C., Foxman B.M., and Deng L. Angew. Chem., Int. Ed. 44 (2005) 105-108
20. Mekonnen A., and Carlson R. Eur. J. Org. Chem. (2006) 2005-2013
21. Kawabata T., Kato M., Mizugaki T., Ebitani K., and Kaneda K. Chem. Eur. J. 11 (2005) 288-297
22. Benati L., Nanni D., and Spagnolo P. J. Chem. Soc., Perkin Trans. 1 (1997) 457-461
23. Benati L., Calestani G., Nanni D., and Spagnolo P. J. Org. Chem. 63 (1998) 4679-4684
24. Benati L., Nanni D., and Spagnolo P. J. Org. Chem. 64 (1999) 5132-5138
25. Benati L., Bencivenni G., Leardini R., Minozzi M., Nanni D., Scialpi R., Spagnolo P., and Zanardi G. J. Org. Chem. 70 (2005) 3046-3053
26. Hakimelahi G.H., and Just G. Synth. Commun. 10 (1980) 429-435
27. Moriarty R.M., Vaid R.K., Ravikumar V.T., Vaid B.K., and Hopkins T.E. Tetrahedron Lett. 44 (1988) 1603-1604
28. Moriarty R.M., Vaid R.K., Ravikumar V.T., Vaid B.K., and Hopkins T.E. Tetrahedron 44 (1988) 1603-1607
29. Sabot C., Kumar K.A., Antheaume C., and Mioskowski C. J. Org. Chem. 72 (2007) 5001-5004
30. Sabot C., Kumar K.A., Meunier S., and Mioskowski C. Tetrahedron Lett. 78 (2007) 3863-3866
31. Ghobril C., Sabot C., Mioskowski C., and Baati R. Eur. J. Org. Chem. (2008) 4104-4108
32. Xie X., Cai G., and Ma D. Org. Lett. 7 (2005) 4693-4695
33. Hamashima, Y.; Ishikura, K.; Kubota, T.; Minami, K. US Patent 4,578,378, 1986.
34. -1; LC-MS (CI): 213 (M+1).
35. -1; LC-MS (APCI): 187 (M+1).
36. -1; LC-MS (APCI): 315 (M+1).