Synthesis of C6-Phosphonated Purine Derivatives
11th Paul Walden Symposium on Organic Chemistry 2019
Kārlis Ēriks Kriķis, Irina Novosjolova

Purine derivatives are widely studied due to their biological activity. They are used as anticancer and antiviral drugs, and as agonists and antagonists of adenosine receptors. Using previously discovered conditions compound 3 was synthesized. Then in CuAAC reaction between azide 3 and different alkynes (phenylacetylene, 5-hexynnitrile, methyl propiolate) bistrizolyl purine derivatives 4 were obtained in yields up to 76%. Next, Arbuzov type reaction has been done using phosphites and bis-triazolylpurine derivatives 4, resulting C6-phosphonated purines 5 with yields up to 67% (Scheme 1). The structure of compound 5 was proved by X-ray analysis (Figure 1).


Keywords
purines, phosphonates, triazoles.

Kriķis, K., Novosjolova, I. Synthesis of C6-Phosphonated Purine Derivatives. In: 11th Paul Walden Symposium on Organic Chemistry, Latvia, Rīga, 19-20 September, 2019. Rīga: 2019, pp.57-57.

Publication language
English (en)
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