1,2,3-Triazoles as Leaving Groups in SNAr–Arbuzov Reactions: Synthesis of C6-Phosphonated Purine Derivatives
12th Paul Walden Symposium on Organic Chemistry: Program and Abstract Book 2021
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. 1 In our studies we proved that 1,2,3-triazoles can be used as leaving groups in SNAr reactions with N-, S-, O-, C-nucleophiles. 2-4 In this research we obtained 2,6-bistriazolylpurine derivatives 3 in CuAAC between diazide 2 and different alkyl-/arylalkynes and used them in reactions with phosphites, obtaining 2-triazolylpurine phosphonates 4 in yields up to 82%. Alternative pathway which starts with SNAr-Arbuzov reaction on 2,6-dichloropurine 1, yields phosphonates 5 and involves next SNAr with NaN3 and subsequent CuAAC did not give the desired products 4 (Scheme 1). Structure of compound 4 was proved by X-ray analysis (Scheme 1).


Keywords
2,6-bis(triazolyl)purines, purine phosphonates, 2-triazolylpurines, nucleophilic aromatic substitution
Hyperlink
https://walden.osi.lv/wp-content/uploads/2021/10/12th_P.Walden_Symposium_Program.Abstract_BOOK.pdf

Kriķis, K., Novosjolova, I. 1,2,3-Triazoles as Leaving Groups in SNAr–Arbuzov Reactions: Synthesis of C6-Phosphonated Purine Derivatives. In: 12th Paul Walden Symposium on Organic Chemistry: Program and Abstract Book, Latvia, Riga, 28-29 October, 2021. Riga: RTU Press, 2021, pp.43-43.

Publication language
English (en)
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