A flexible three-component synthesis of novel δ-amino acids incorporating an imidazo[1,2-a]pyridine backbone

Synthesis

Volumn , Issue 16, 2006, Pages 2677-2684

  Veljkovic, Ivana ^a   Zimmer, Reinhold ^a   Reissig, Hans Ulrich ^a   Brüdgam, Irene ^a   Hartl, Hans ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Amino acids; Cyclopropanes; Lactams; Peptides; Pyridines

Indexed keywords

CATALYST ACTIVITY; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL);

CYCLOPROPANES; LACTAMS; PEPTIDES; PYRIDINES;

AMINO ACIDS;

1 BENZYL 3,4,4 TRIMETHYL 3,4 DIHYDRO 1H DIPYRIDO[1,2 A;3',2' D]IMIDAZOL 2 ONE; 1 BENZYL 4,4 DIMETHYL 3,4 DIHYDRO 1H DIPYRIDO[1,2 A;3',2' D]IMIDAZOL 2 ONE; 2 AMINOPYRIDINE; ALANINE DERIVATIVE; AMINO ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYANIDE; IMIDAZO[1,2 A]PYRIDINE; IMIDAZOLE DERIVATIVE; ISONITRILE DERIVATIVE; METHYL 2TRIMETHYLSILOXYCYCLOPROPANECARBOXYLATE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 33748324475     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942506     Document Type: Article

References (36)

1. Sewald, N.; Jakubke, H.-D. Peptides: Chemistry and Biology; Wiley-VCH: Weinheim, 2002, Chap. 7.
2. For excellent up to date reviews, see: (a) Zhu, J.; Bienaymé, H. Multicomponent Reactions; Wiley-VCH: Weinheim, 2005.
3. (b) Dömling, A. Chem. Rev. 2006, 106, 17.
4. (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133.
5. (d) Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168;
6. Angew. Chem. 2000, 118, 3300.
7. (e) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321.
8. (f) Ugi, I.; Lohberger, S.; Karl, R. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Chap. 4.6.
9. (g) Ugi, I. J. Prakt. Chem. 1997, 339, 499.
10. (a) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151.
11. (b) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73.
12. Zimmer, R.; Ziemer, A.; Gruner, M.; Brüdgam, I.; Hartl, H.; Reissig, H.-U. Synthesis 2001, 1649.
13. Veljkovic, I.; Al-Ajmi, H.; Özbek, H.; Reissig, H.-U., manuscript in preparation.
14. (a) Groebke, K.; Weber, L.; Mehlin, F. Synlett 1998, 661.
15. (b) Mandair, G. S.; Light, M.; Russell, A.; Hursthouse, M.; Bradley, M. Tetrahedron Lett. 2002, 43, 4267.
16. (c) Lyon, M. A.; Kercher, T. S. Org. Lett. 2004, 6, 4989.
17. (d) Blackburn, C.; Guan, B.; Fleming, P.; Shiosaki, K.; Tsai, S. Tetrahedron Lett. 1998, 39, 3635.
18. Alternative methods for the preparation of imidazo[1,2-a]pyridines: (e) Krasovsky, A. L.; Nenajdenko, V. G.; Balenkova, E. S. Synthesis 2002, 1379.
19. (a) Katritzky, A. R.; Xu, Y.-J.; Tu, H. J. Org. Chem. 2003, 68, 4935.
20. (b) Jaramillo, C.; de Diego, E.; Hamdouchi, C. Synlett 2002, 1544; and references cited therein.
21. (a) Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250;
22. Angew. Chem. 2004, 116, 6408.
23. (b) Loupy, A. Microwaves in Organic Synthesis; Wiley-VCH: Weinheim, 2002.
24. For microwave-assisted synthesis of fused 3-aminoimidazolines, see: (c) Ireland, S. M.; Tye, K.; Whittaker, M. Tetrahedron Lett. 2003, 44, 4369.
25. (d) Varma, R. S.; Kumar, D. Tetrahedron Lett. 1999, 40, 7665.
26. Blackburn, C.; Guan, B. Tetrahedron Lett. 2000, 41, 1495.
27. Högberg, T.; Ström, P.; Ebner, M.; Rämsby, S. J. Org. Chem. 1987, 52, 2033.
28. Hünig, S.; Schaller, R. Angew-Chem., Int. Ed. Engl. 1982, 21, 36;
29. Angew. Chem. 1982, 94, 1.
30. (a) Campagne, J.-M.; Coste, J.; Jouin, P. J. Org. Chem. 1995, 60, 5214.
31. (b) Castro, B.; Dormoy, J. R.; Evin, G.; Selve, C. Tetrahedron Lett. 1975, 1219.
32. Carpino, L. A.; El-Faham, A. J. Am. Chem. Soc. 1995, 117, 5401.
33. Kunkel, E.; Reichelt, I.; Reissig, H.-U. Liebigs Ann. Chem. 1984, 512.
34. Casanova, J.; Newton, D. W.; Schuster, R. E. J. Am. Chem. Soc. 1966, 88, 3473.
35. Sheldrick, G. M. SHELX97 (Includes SHELXS97, SHELXL97, CIFTAB) Programs for Crystal Structure Analysis (Release 97-2); Universität Göttingen: Germany, 1998.
36. Atomic coordinates and further crystallographic details have been deposited at the Cambridge Crystallographic Data Centre, deposition number CCDC 601760, and copies of this data can be obtained in application to CCDC, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK (fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk).