1013022-33-7Relevant articles and documents
Triphenylphosphine-free approach for one-pot N-alkylation of purine, pyrimidine, and azole derivatives with alcohols using P2O5/KI: A facile and selective route to access carboacyclic nucleosides
Behrouz, Somayeh,Soltani Rad, Mohammad Navid,Ahmadi, Samira
supporting information, (2019/08/12)
A facile, selective, and mild synthetic approach for one-pot N-alkylation of nucleobases and other related N-heterocycles via alcohols, using a mixture of P2O5 and KI is described. The reaction of structurally diverse purines, pyrimidines, and/or azoles with primary alcohols with the use of P2O5/KI and basic mixture of Et3N/K2CO3 in refluxing DMF affords the corresponding N-alkyl derivatives (carboacyclic nucleosides) in good to reasonable yields. The influence of different parameters comprising solvent, base, temperature, and substrate/reagent ratios was assessed on the reaction progress. The secondary and tertiary alcohols were failed to react with nucleobases. The main advantageous of current protocol is formation of water soluble side products in which provides simple work-up and purification processes.
Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohols in bmim[Br]: A rapid route to access acyclic nucleosides
Rad, Mohammad Navid Soltani,Behrouz, Somayeh,Zarenezhad, Elham,Kaviani, Narjes
, p. 1603 - 1612 (2015/07/07)
Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohol in ionic liquid media as a straightforward route to access acyclic nucleoside was described. In this protocol purine, pyrimidine as well as azole derivatives underwent the N-a
One-pot synthesis of N-alkyl purine and pyrimidine derivatives from alcohols using TsIm: a rapid entry into carboacyclic nucleoside synthesis
Soltani Rad, Mohammad Navid,Khalafi-Nezhad, Ali,Behrouz, Somayeh,Faghihi, Mohammad?Ali,Zare, Abdolkarim,Parhami, Abolfath
, p. 1778 - 1785 (2008/09/18)
A convenient and efficient one-pot N-alkylation of nucleobases from alcohols using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, treatment of alcohols with a mixture of purine or pyrimidine nucleobase, TsIm, K2CO3, and triethylamine in refluxing DMF regioselectively furnishes the corresponding N-alkyl nucleobases in good yields. This methodology is highly efficient for various structurally diverse primary alcohols.