Synthesis of 2-Triazolyl Purine C6 Phosphonates in SNArArbuzov Reaction
Materials Science and Applied Chemistry 2020 2020
Kārlis Ēriks Kriķis, Irina Novosjolova

Purines and their derivatives show wide spectra of biological activities. They are widely used as antiviral and anticancer drugs. From the literature it is known that modification with phosphonate1 and triazolyl2 moieties could lead to novel class of biologically active compounds. To obtain the target phosphonate derivatives, firstly 2,6-diazidopurine 2 was obtained using a sequence of Mitsunobu and SNAr reactions. Then 2,6-bis-1,2,3-triazolylpurine derivatives 3 were synthesized via copper(I) catalysed azide-alkyne cycloaddtion (CuAAC) between diazide 2 and different alkyl/aryl/heteroaryl alkynes. Finally, 2-triazolyl C6 phosphonates 4 were obtained in SNAr-Arbuzov type reaction between bistriazoles 3 and P(OEt)3, using triazolyl ring at C6 position of purine as a good leaving group3 (Scheme 1). The structure of compound 4 was proved by X-ray analysis (Fig. 1).


Keywords
Purine, SnAr reaction, Arbuzov reaction C6-phosphonates

Kriķis, K., Novosjolova, I. Synthesis of 2-Triazolyl Purine C6 Phosphonates in SNArArbuzov Reaction. In: Materials Science and Applied Chemistry 2020, Latvia, Rīga, 23-23 October, 2020. Rīga: 2020, pp.55-55.

Publication language
English (en)
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