Enamine - smart chemistry solutions
PRODUCTS


Functionalized Azides
Download printable article in pdf-format

Organic azides are an important class of synthetic building blocks. In organic chemistry azides are commonly used for introducing an amino-group via Staudinger reaction. With the recent advent of "click-chemistry" azides became enormously popular for their participation in the Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction1. Because of the high rate of synthetic success of both Huisgen cycloaddition and Staudinger reduction these reactions are often used in combinatorial and medicinal chemistry. Enamine presented the set of azides suitable for click-chemistry transformations earlier.

Building blocks capable of linking of low molecular weight compounds in chemically and stereochemically predefined manners are one of the major demands of both high throughput parallel synthesis and fragment-based lead discovery. In this connection azides bearing additional functional groups are especially attractive building blocks. For example, 2-tosyloxyethyl azide was successfully employed in the preparation of analogues of nucleosides and nucleotides2, amino acids functionalized with metal ligands 13, biologicaly potent vicinal diamines4, and bimodal MR-PET contrast agents5. Different amino-functionalized azides were used for the "click-to-chelate" installation of metal chelates 2 into biomolecules for radiolabeling6 and in the synthesis of D3 selective dopamine receptors 37. Azides bearing other functional groups were employed in the preparation of potent inhibitors of NAD synthesis 48 and for in-situ selection of lead compounds by click-chemistry9. Besides medicine-oriented syntheses functionalized azides were used as key building blocks for efficient synthesis of polyamines10, asymmetric vicinal diamines, and [n]rotaxanes11.

 

Derivatives of functionalized azides

 

Given this synthetic potential we have generated a collection of functionalized azides. The collection contains both known and novel compounds. You can download the database of offered functionalized azides in ISIS DB format. Examples of available functionalized azides are presented below.

EN300-43962EN300-44256EN300-44910
EN300-52518EN300-53030EN300-53031
EN300-54801 EN300-56456EN300-59236
EN300-61301EN300-62370EN300-62412
EN300-63896 EN300-64856EN300-53030
 
 
1. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. 2001, 40, 2004–2021.

2. F. Amblard, J. H. Cho, R. F. Schinazi, Chem. Rev. 2009, 109, 4207–4220.

3. A. Nadler, C. Hain, U. Diederichsen, Eur. J. Org. Chem. 2009, 4593–4599.

4. T. L. Micotto, A. S. Brown, J. N. Wilson, Chem. Commun. 2009, 7548–7550.

5. L. Frullano, C. Catana, T. Benner, A. D. Sherry, P. Caravan, Angew. Chem. Int. Ed. 2010, 49, 2382–2384.

6. T. L. Mindt, H. Struthers, L. Brans, T. Anguelov, C. Schweinsberg, V. Maes, D. Tourwe, R. Schibli, J. Am. Chem. Soc. 2006, 128, 15096-15097.

7. M. Dorfler, N. Tschammer, K. Hamperl, H. Hubner, P. Gmeiner, J. Med. Chem. 2008, 51, 6829–6838.

8. G. Colombano, C. Travelli, U. Galli, A. Caldarelli, M. G. Chini, P. L. Canonico, G. Sorba, G. Bifulco, G. C. Tron, A. A. Genazzani, J. Med. Chem. 2010, 53, 616–623.

9. A. Krasinski, Z. Radic, R. Manetsch, J. Raushel, P. Taylor, K. B. Sharpless, H. C. Kolb, J. Am. Chem. Soc. 2005, 127, 6686-6692.

10. B. Carboni, A. Benalil, M. Vaultier, J. Org. Chem. 1993, 58, 3736-3741.

10. D. Tuncel, M. Katterle, Chem. Eur. J. 2008, 14, 4110–4116.



© 1991 - 2018 ENAMINE
Terms of Use | Privacy Policy | Cookies Policy