Synthesis of tetrazolopiperazine building blocks by a novel multi-component reaction

Tetrahedron Letters

Volumn 45, Issue 34, 2004, Pages 6421-6424

  Umkehrer, Michael ^a,b   Kolb, Jürgen ^a   Burdack, Christoph ^a   Ross, Günther ^a   Hiller, Wolfgang ^b  

^a Priaton GmbH   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Combinatorial chemistry; Isocyanoethyltosylate; Tetrazolopiperazines; Ugi reaction

Indexed keywords

2 ISOCYANOETHYLTOSYLATE; ALDEHYDE; AMINE; CYANIDE; PIPERAZINE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; QUANTUM YIELD;

EID: 4243141892     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.06.133     Document Type: Article

References (19)

1. M.A. Gallop, R.W. Barrett, W.J. Dower, S.P.A. Fodor, and E.M. Gordon J. Med. Chem. 37 1994 1233
2. E.M. Gordon, R.W. Barrett, W.J. Dower, S.P.A. Fodor, and M.A. Gallop J. Med. Chem. 37 1994 1385
3. A. Dömling Comb. Chem. High Throughput Screen. 1 1998 1
4. A. Dömling, and I. Ugi Angew. Chem. 112 2000 3300
5. A. Dömling, I. Ugi, and W. Hörl Endeavour 18 1994 115
6. T.A. Keating, and R.W. Armstrong J. Am. Chem. Soc. 118 1996 2574
7. I. Ugi, and C. Steinbrückner Chem. Ber. 94 1961 734
8. D. Lee, J.K. Sello, and S.L. Schreiber Org. Lett. 2 2000 709
9. J. Zhu Eur. J. Org. Chem. 2003 1133
10. R.V.A. Orru, and M. de Greef Synthesis 2003 1471
11. Towards the ideal synthesis: P.A. Wender, S.T. Handy, and D.L. Wright Chem. Ind. 1 1997 795
12. L. Weber, K. Illgen, and M. Almstetter Synlett 3 1999 366
13. Th. Nixey, M. Kelly, and Ch. Hulme Tetrahedron Lett. 41 2000 8729
14. I. Ugi Angew. Chem., Int. Ed. Engl. 1 1962 8
15. I. Ugi, and C. Steinbruckner Chem. Ber. 94 1961 734
16. H. Bienayme, and K. Bouzid Tetrahedron Lett. 39 1998 2735
17. 4 and concentrated in vacuo. The resulting oil is purified by column chromatography on silica gel (hexane/ethyl acetate)
18. Compound 5a was isolated in 49% yield as a white solid
19. D.S. Matteson, and R.A. Bailey J. Am. Chem. Soc. 90 1968 3761