The Use of Azide-Tetrazole Equilibrium in the Modification of Fused Pyrimidines

International Symposium on Synthesis and Catalysis 2023 (ISySyCat 2023): Book of Abstracts 2023
Jānis Miķelis Zaķis, Kristaps Leškovskis, Dāgs Dāvis Līpiņš, Zigfrīds Kapilinskis, Dinesh Kumar, Anna Dozorina, Jurijs Renārs Vērdiņš, Anatoly Mishnev, Māris Turks, Irina Novosjolova

By utilizing various nucleophiles and the presence of azide-tetrazole equilibrium in structure 2, we have established a unique approach toward imidazolyl/pyrrolyl/aryl tetrazole derivatives 3a–c (Scheme 1). In our case, the tetrazole ring acts initially as a protecting group, encouraging nucleophiles to attach to the less active C2 position of fused pyrimidine. Then it acts as a leaving group when the pyrimidine ring undergoes a second nucleophile attack, eventually leading to the formation of tetrazolyl derivatives 3. We have confirmed the structures of these compounds using X-ray analysis. Besides, the opened products can be used as starting materials to prepare diazepine-type structures.

Atslēgas vārdi
purine, azide, tetrazole, fused pyrimidines, ring opening

Zaķis, J., Leškovskis, K., Līpiņš, D., Kapilinskis, Z., Kumar, D., Dozorina, A., Vērdiņš, J., Mishnev, A., Turks, M., Novosjolova, I. The Use of Azide-Tetrazole Equilibrium in the Modification of Fused Pyrimidines. No: International Symposium on Synthesis and Catalysis 2023 (ISySyCat 2023): Book of Abstracts, Portugāle, Evora, 5.-8. septembris, 2023. Evora: 2023, P52.-P52.lpp.

Publikācijas valoda
English (en)