Rapid microwave-assisted preparation of amino-functionalized polymers

Tetrahedron Letters

Volumn 49, Issue 42, 2008, Pages 6108-6110

  Ljungdahl, Natalie ^a   Martikainen, Laura ^a   Kann, Nina ^a  

^a CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; HALIDE; PHTHALIMIDE; POLYMER; TRIPHENYLPHOSPHINE;

AMINATION; ARTICLE; METHODOLOGY; MICROWAVE RADIATION; REACTION TIME; RING OPENING; SUBSTITUTION REACTION;

EID: 50549093410     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.08.009     Document Type: Article

References (30)

1. For a recent report concerning the preparation of non-PEG derived polyether resin gels with an aminobutyl-functionality, and their application in synthesis, see:. Cavalli G., Shooter A.G., Pears D.A., Wellings D.A., Gulzar S., and Steinke J.H.G. J. Comb. Chem. 9 (2007) 1012-1027
2. Rich D.H., and Gurwara S.K. J. Am. Chem. Soc. 97 (1975) 1575-1579
3. Mitchell A.R., Kent S.B.H., Erickson B.W., and Merrifield R.B. Tetrahedron Lett. (1976) 3795-3798
4. Weinshenker N.M., and Shen C.-M. Tetrahedron Lett. (1972) 3281-3284
5. Mitchell A.R., Erickson B.W., Ryabtsev M.N., Hodges R.S., and Merrifield R.B. J. Am. Chem. Soc. 98 (1976) 7357-7362
6. Sparrow J.T. J. Org. Chem. 41 (1976) 1350-1353
7. Góźdź A.S. Polym. Bull. 5 (1981) 591-595
8. Reaction of unfunctionalized polystyrene resin is an alterative method of introducing the phthalimide moiety, see Ref. 3 as well as:. Zikos C.C., and Ferderigos N.G. Tetrahedron Lett. 36 (1995) 3741-3744
9. Meisenbach M., Allmendinger T., and Mak C.-P. Org. Process Res. Dev. 7 (2003) 553-558
10. For an alternative approach introducing the amino-functionality in the form of diallylamine, see:. Garro-Helion F., Merzouk A., and Guibé F. J. Org. Chem. 58 (1993) 6109-6113
11. For an amidomethylation approach, see:. Lee T.-K., Ryoo S.-J., Byun J.-W., Lee S.-M., and Lee Y.-S. J. Comb. Chem. 7 (2005) 170-173
12. Kappe C.O., and Stadler A. Microwaves in Organic and Medicinal Chemistry (2005), Wiley-VCH, Weinheim
13. In: Loupy A. (Ed). Microwaves in Organic Synthesis (2002), Wiley-VCH, Weinheim
14. In: Lidström P., and Tierney J.P. (Eds). Microwave-Assisted Organic Synthesis (2005), Blackwell Publishing, Oxford
15. Vaultier M., Knouzi N., and Carrié R. Tetrahedron Lett. 24 (1983) 763-764
16. Knouzi N., Vaultier M., and Carrié R. Bull. Chem. Soc. Fr. (1985) 815-819
17. Durand P., Richard P., and Renault P. J. Org. Chem. 63 (1998) 9723-9727
18. Carrington S., Renault J., Tomasi S., Corbel J.-C., Uriac P., and Blagbrough I.S. Chem. Commun. (1999) 1341-1342
19. Murata A., and Wada T. Tetrahedron Lett. 47 (2006) 2147-2150
20. For examples of microwave-assisted click reactions, see:. Katritzky A.R., and Singh S.K. J. Org. Chem. 67 (2002) 9077-9079
21. Khanetskyy B., Dallinger D., and Kappe C.O. J. Comb. Chem. 6 (2004) 884-892
22. Appukkuttan P., Dehaen W., Fokin V.V., and Van der Eycken E. Org. Lett. 6 (2004) 4223-4225
23. Baillez V., Olesker A., and Cleophax J. Tetrahedron 60 (2004) 1079-1085
24. Busscher G.F., Groothuys S., de Gelder R., Rutjes F.P.J.T., and van Delft F.L. J. Org. Chem. 69 (2004) 4477-4481
25. Liao M., Duan X., and Liang Y. Tetrahedron Lett. 46 (2005) 3469-3472
26. Carpino L.A., and Han G.Y. J. Org. Chem. 37 (1972) 3404-3409
27. Arad O., and Houghten R.A. Pept. Res. 3 (1990) 42-50
28. For an alternative procedure, see also:. Bunin B. The Combinatorial Index (1998), Academic Press, San Diego pp 217-218
29. -1) and compared to the initial loading of the resin.
30. For applications of amino-functionalized resins, see:. Olsen C.A., Franzyk H., and Jaroszewski J.W. Synthesis (2005) 2631-2653