Annulation of primary amines to piperazines and diazaspirocycles utilizing α-methyl benzyl resin

Journal of Combinatorial Chemistry

Volumn 8, Issue 1, 2006, Pages 132-140

  Macleod, Calum ^a,b   Martinez Teipel, Blanca I ^a   Barker, William M ^a   Dolle, Roland E ^a  

^a ADOLOR CORPORATION   (United States)

^b Argenta Discovery Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBAMIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; MESYLIC ACID DERIVATIVE; PIPERAZINE DERIVATIVE; RESIN; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

AMINES; AZA COMPOUNDS; CARBAMATES; COMBINATORIAL CHEMISTRY TECHNIQUES; MAGNETIC RESONANCE SPECTROSCOPY; MESYLATES; MOLECULAR STRUCTURE; PIPERAZINES; RESINS, SYNTHETIC; SPIRO COMPOUNDS;

EID: 31544433452     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc050106w     Document Type: Article

References (23)

1. Dolle, R. E.; Macleod, C.; Martinez-Teipel, B. I.; Barker, W. M.; Seida, P.; Herbetz, T. Angew. Chem., Int. Ed. 2005, 44, 5830-5833. The acronym SPAn (derived from solid/ solution-phase annulation) collectively refers to the reagents, products, and technology thereof for primary amine annulation.
2. (a) Ye, B.; Chou, Y.-L.; Karanjawala, R.; Lee, W.; Lu, S.-F.; Shaw, K. J.; Jones, S.; Lentz, D.; Liang, A.; Tseng, J.-L.; Wu, Q.; Zhao, Z. Bioorg. Med. Chem. Lett. 2004, 14, 761-765.
3. (b) Raviña, E.; Casariego, I.; Masaguer, C. F.; Fontenla, J. A.; Montenegro, G. Y.; Rivas, M. E.; Loza, M. I.; Enguix, M. J.; Villazon, M.; Cadavid, M. I.; Demontis, G. C. J. Med. Chem. 2000, 43, 4678-4693.
4. (c) Rival, Y.; Hoffmann, R.; Didier, B.; Rybaltchenko, V.; Bourguignon, J.-J.; Wermuth, C. G. J. Med. Chem. 1998, 41, 311-317.
5. (d) Naylor, A.; Judd, D. B.; Lloyd, J. E.; Scopes, D. I. C.; Hayes, A. G.; Birch, P. J. J. Med. Chem. 1993, 36, 2075-2083.
6. Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893-930.
7. (a) Hu, X. E.; Kim, N. K.; Gray, J. L.; Almstead, L.-I. K.; Seibel, W. L.; Ledoussal, B. J. Med. Chem. 2003, 46, 3655-3661.
8. (b) Smyth, M. S.; Rose, J.; Mehrotra, M. M.; Heath, J.; Ruhter, G.; Schotten, T.; Seroogy, J.; Volkots, D.; Pandy, A.; Scarborough, R. M. Bioorg. Med. Chem. Lett. 2001, 11, 1289-1292.
9. Salvino, J. M.; Gerard, B.; Ye, H.-F.; Sauvagnat, B.; Dolle, R. E. J. Comb. Chem. 2003, 5, 260-266, and references therein.
10. Nefzi, A.; Giulianotti, M. A.; Houghten, R. A. Tetrahedron Lett. 1999, 40, 8539-8542.
11. Conti, P.; Demont, D.; Cals, H.; Ottenheijm, H. C. J.; Leysen, D. Tetrahedron Lett. 1997, 38, 2915-2918.
12. (a) Nugiel, D. A.; Cornelius, L. A. M.; Corbett, J. W. J. Org. Chem. 1997, 62, 201-203.
13. (b) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317-8320.
14. Dixit, D. M.; Leznoff, C. C. J. Chem. Soc., Chem. Commun. 1977, 798-799.
15. Hernández, A.; Hodges, J. C. J. Org. Chem. 1997, 62, 3153-3157.
16. +)].
17. 3OD): δ 6.70-6.90 (2H, d) and 7.10-7.30 (2H, d).
18. (a) Phoon, C. W.; Sim, M. M. Synlett 2001, 5, 697-699.
19. (b) Harju, K.; Vahermo, M.; Mutikainen, I.; Yli-Kauhaluoma, J. J. Comb. Chem. 2003, 5, 826-833.
20. Barlos, K.; Gatos, D.; Hondrelis, J.; Matsoukas, J.; Moore, G. J.; Schäfer, W.; Sotiriou, P. Liebigs Ann. Chem. 1989, 951-955.
21. Shannon, S. K.; Barany, G. J. Comb. Chem. 2004, 6, 165-170.
22. Fissher, M. J.; Jakubowski, J. A.; Masters, J. A.; Mullaney, J. T. PCT Int. Appl. WO 97/11940, 1997.
23. -1.