- 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
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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.
- Behrouz, Somayeh,Soltani Rad, Mohammad Navid,Ahmadi, Samira
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supporting information
(2019/08/12)
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- One-pot protocol for N-alkylation of purine, pyrimidine and azole derivatives via alcohols using Ph3P/I2: simple route for carboacyclic nucleoside synthesis
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A simple and efficient synthetic protocol for the one-pot N-alkylation of nucleobases and their related N-heterocycles via alcohols utilizing the combination of PPh3and I2is reported. In this protocol purine, pyrimidine and azole derivatives underwent the N-alkylation reaction with diverse primary alcohols using Ph3P/I2in the presence of Et3N-K2CO3in anhydrous DMF to give the N-alkyl adducts (carboacyclic nucleosides) in good yields (up to 90%). The influence of some parameters in this reaction including type of solvent, base, reagents and temperature was discussed. In addition, this protocol has proved the favorable selectivity towards primary hydroxyl versus secondary hydroxyl group in diols.
- Soltani Rad, Mohammad Navid,Soleimani, Faezeh
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supporting information
p. 4947 - 4953
(2016/07/19)
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- Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohols in bmim[Br]: A rapid route to access acyclic nucleosides
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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
- Rad, Mohammad Navid Soltani,Behrouz, Somayeh,Zarenezhad, Elham,Kaviani, Narjes
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p. 1603 - 1612
(2015/07/07)
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- One-pot synthesis of n-alkyl purine, pyrimidine and azole derivatives from alcohols using ph3p/ccl4: A rapid route to carboacyclic nucleoside synthesis
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A facile and efficient method for one-pot N-alkylation of nucleobases and azole derivatives from alcohols using triphenylphosphine in carbon tetrachloride is described. In this method, treatment of alcohols with a mixture of triphenylphosphine, carbon tetrachloride, nucleobase or azole derivatives and potassium carbonate in the presence of catalytic amounts of tetra-n- butylammonium iodide (TBAI) in refluxing N,N-dimethylformamide, furnishes the corresponding N-alkyl derivatives in good yields. This methodology is highly efficient for various structurally diverse primary alcohols and also useful for N-alkylation of other N-heterocycles containing an acidic N-H bond.
- Rad, Mohammad Navid Soltani,Khalafi-Nezhad, Ali,Behrouz, Somayeh,Asrari, Zeinab,Behrouz, Marzieh,Aminia, Zohreh
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experimental part
p. 3067 - 3076
(2009/12/28)
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- One-pot synthesis of N-alkyl purine and pyrimidine derivatives from alcohols using TsIm: a rapid entry into carboacyclic nucleoside synthesis
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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.
- Soltani Rad, Mohammad Navid,Khalafi-Nezhad, Ali,Behrouz, Somayeh,Faghihi, Mohammad?Ali,Zare, Abdolkarim,Parhami, Abolfath
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p. 1778 - 1785
(2008/09/18)
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