Triazenes as robust and simple linkers for amines in solid-phase organic synthesis

Tetrahedron Letters

Volumn 40, Issue 11, 1999, Pages 2105-2108

  Bräse, Stefan ^a   Köbberling, Johannes ^a   Enders, Dieter ^a   Lazny, Ryszard ^a,c   Wang, Mingfei ^a   Brandtner, Siegfried ^b  

^a UNIVERSITY HOSPITAL RWTH AACHEN   (Germany)

^b DDTeC GmbH   (Germany)

^c UNIVERSITY OF BIALYSTOK   (Poland)

Author keywords

Amines; Protecting groups; Solid phase synthesis; Triazenes

Indexed keywords

TRIAZENE DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033548667     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00160-4     Document Type: Article

References (39)

1. Part 3 in the Series: Nitrogen-based Linker. A part of this work has been presented at Schliersee conference, October 1998. For part 1, see ref. [35]. For part 2, see ref. [36].
2. Gordon EM, Barrett RW, Dower WJ, Fodor SPA, Gallop MA. J. Med. Chem. 1994;37:1385-1401.
3. Ellman J. Acc. Chem. Res. 1996;29:132-143.
4. Armstrong RW, Combs AP, Tempest PA, Brown SD, Keating TA. Acc. Chem. Res. 1996;29: 123-131.
5. Balkenhohl F, von dem Bussche-Hünnefeld C, LAnsky A, Zechel C. Angew. Chem. Int. Ed. Engl. 1996;35:2289-2337.
6. Früchtel, JS, Jung G. In G. Jung (Ed.) 1996, Combinatorial Peptide and Nonpeptide Libraries: A Handbook, (pp. 19-78). VCH, Weinheim, Germany.
7. Hermkens PHH, Ottenheijm HCJ, Rees D. Tetrahedron 1996;52:4527-4554.
8. Kyle DJ. Drug Disc. Today 1997;2:229-234.
9. Wallace RW. Drug Disc. Today 1997;2:355-355.
10. Burbaum JJ, Sigal NH. Curr. Opin. Chem. Biol. 1997;1:72-78.
11. Meisenbach M, Voelter W. Chem. Lett 1997:1265-1266.
12. Aisina J, Rabanal F, Giralt E, Albericio F. Tetrahedron Lett 1994;35, 9633-9636.
13. Bannwarth W, J. H, Barner R. Bioorg. Med. Chem. Lett. 1996,;6: 1525-1528.
14. Dressman BA, Spangle LA, Kaldor SW. Tetrahedron Lett. 1996;37:937-940.
15. Kaljuste K, Unden A. Tetrahedron Lett 1996;35:3031-3034.
16. Gouilleux L, Fehrentz JA, Winternitz F, Martinez J. Tetrahedron Lett. 1996;37:7031-7034.
17. Boojamra CG, Burow KM, Thompson LA, Ellman JA. J. Org. Chem. 1997;62,:1240-1256.
18. Brown AR, Rees DC, Rankovic Z, Morphy JR. J. Am. Chem. Soc. 1997;119,:3288-3295.
19. Hernandez AS, Hodges JC. J. Org. Chem. 1997;38:4861-4864.
20. Ngu K, Patel DV. Tetrahedron Lett. 1997;38:973-976.
21. Ho CY, Kukla MJ. Tetrahedron Lett. 1997;38:2799-2802.
22. Furth PS, Reitman MS, Cook AF. Tetrahedron Lett. 1997;38:5403-5406.
23. Swayze EE. Tetrahedron Lett. 1997;38:8465-8468.
24. Conti P, Demont D, Cals J, Ottenheijm HCJ, Leysen D. Tetrahedron Lett. 1997;38:2915-2918.
25. Kay C, Murray PJ, Sandow L, Holmes AB. Tetrahedron Lett. 1997;39:6941-6944.
26. Hird NW, Irie K, Nagai K. Tetrahedron Lett. 1997;38:7111-7114.
27. Filzpatrick LJ, Rivero RA. Tetrahedron Lett. 1997;38:7479-7482.
28. Hsieh H, Wu Y, Chen S, Wang K. Chem. Commun. 1998:649-650.
29. Dressman B, Singh U, Kaldor S. Tetrahedron Lett. 1998;39:3631-3634.
30. Lorsbach BK, Bagdanoff JT, Miller RB, Kurth MJ. J. Org. Chem. 1998;63:2244-2250.
31. Estep KG, Neipp CE, Stramiello LMS, Adam MD, Allen MP, Robinson S, Roskamp EJ. J. Org. Chem. 1998;63:5300-5301.
32. Breitenbucher JG, Johnson CR, Haight M, Phelan JC. Tetrahedron Lett. 1998;39:1295-1298.
33. Del Fresno M, Alsina J, Royo M, Barany G, Albericio F. Tetrahedron Lett. 1998;39:2639-2642.
34. Chhabra S, Khan A, Bycroft B. Tetrahedron Lett 1998;39:3585-3588.
35. Bräse S, Enders D, Köbberling J, Avemaria F. Angew. Chem. Int. Ed. Engl. 1998;37:3413-3415.
36. Bräse S, Köbberling J, Enders D, Lazny R, Poplawski J. Synlett, submitted.
37. m-Hydroxyaniline is more stable towards alkaline solution than the ortho and para derivative.
38. The yields are based on the elemental analysis of the product resin. All new non-polymeric compounds have been characterized by NMR, MS, IR and elemental analysis or HRMS, respectively. The resins have been characterized by elemental analysis and IR.
39. Bräse S, Dahmen S. Unpublished results .