A novel tandem process leading to functionalized glutarimides

Tetrahedron Letters

Volumn 46, Issue 15, 2005, Pages 2611-2614

  Popović Dordević, Jelena B ^a   Ivanović, Milovan D ^b   Kiricojević, Vesna D ^c  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

^c UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

Functionalized or spirobicyclic glutarimides; Synthesis; Tandem process

Indexed keywords

AMIDE; CARBENOID; GLUTARIMIDE DERIVATIVE;

ACYLATION; ARTICLE; CATALYSIS; MICHAEL ADDITION; SYNTHESIS;

EID: 15244347524     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.087     Document Type: Article

References (26)

1. D.J. Bennett, A.J. Blake, P.A. Cooke, C.R.A. Godfrey, P.L. Pickering, N.S. Simpkins, M.D. Walker, and C. Wilson Tetrahedron 60 2004 4491 4511
2. C.-Y. Chen, B.-R. Chang, M.-R. Tsai, M.-Y. Chang, and N.-C. Chang Tetrahedron 59 2003 9383 9387 and references cited therein
3. I. Ibnusaud, and G. Thomas Tetrahedron Lett. 44 2003 1247 1249
4. Callewaert, G. Leo. WO 2002068416 A2 ; Chem. Abs. 137:216939
5. M.-Y. Chang, S.-T. Chen, and N.-C. Chang Tetrahedron 58 2002 3623 3628
6. H. Yoda, T. Egawa, and K. Takabe Tetrahedron Lett. 44 2003 1643 1646
7. M. Oba, S. Koguchi, and K. Nishiyama Tetrahedron 58 2002 9359 9363
8. B.E. Maryanoff, H.-C. Zhang, J.H. Cohen, I.J. Turchi, and C.A. Maryanoff Chem. Rev. 104 2004 1431 1628
9. J. Heerklotz, A. Linden, and M. Hesse Tetrahedron 56 2000 7205 7210
10. The Merck Index 13th ed. 2001 Merck & Co. NJ
11. P.A. Grieco, K.J. Henry, J.J. Nunes, and J.E. Matt Jr. J. Chem. Soc., Chem. Commun. 4 1992 368 370
12. C. Gaul, J.T. Njardarson, D. Shan, D.C. Dorn, K.-D. Wu, W.P. Tong, X.-Y. Huang, M.A.S. Moore, and S.J. Danishefsky J. Am. Chem. Soc. 126 2004 11326 11337
13. S.A. Dandekar, S.N. Greenwood, T.D. Greenwood, S. Mabic, J.S. Merola, J.M. Tanko, and J.F. Wolfe J. Org. Chem. 64 1999 1543 1553
14. A. Leonardi, D. Barlocco, F. Montesano, G. Cignarella, G. Motta, R. Testa, E. Poggesi, M. Seeber, P.G. De Benedetti, and F. Fanelli J. Med. Chem. 47 2004 1900 1918
15. W.W.K.R. Mederski, M. Baumgarth, M. Germann, D. Kux, and T. Weitzel Tetrahedron Lett. 44 2003 2133 2136
16. S.N. Osipov, P. Tsouker, L. Hennig, and K. Burger Tetrahedron 60 2004 271 274
17. Crowe, D.; Jones, D. A. WO 2001014335 A1; Chem. Abs. 134:207718
18. T. Hikaru, Y. Kazunori, I. Katsuhiro, T. Hiroki, and M. Shun-Ichi Angew. Chem., Int. Ed. 42 2003 3302 3304
19. R.B. Grossman, D.S. Pendharkar, R.M. Rasne, and M.A. Varner J. Org. Chem. 65 2000 3255 3258
20. C.-Y. Chen, M.-Y. Chang, R.-T. Hsu, S.-T. Chen, and N.-C. Chang Tetrahedron Lett. 44 2003 8627 8630 and references cited therein
21. C. Chuit, R.J.P. Corriu, R. Perz, and C. Reye Tetrahedron 42 1986 2293 2301
22. All new compounds according to detailed structure and substructure searches of Chemical Abstracts via SciFinder. Structurally related glutarimides were reported previously by other routes, see Refs. 1,3, and 16
23. 13C NMR spectra, see Supplementary data
24. Prepared by a modification of a known literature procedure A.P. Krapcho, J. Diamanti, C. Cayen, and R. Bingham Org. Synth., Coll. 5 1973 198
25. 13C NMR, DEPT, and MS spectra are given in the Supplementary data
26. 13C NMR, DEPT, and MS spectra (given in the Supplementary data).