1013022-27-9Relevant articles and documents
Chitosan–silica sulfate nanohybrid: a highly efficient and green heterogeneous nanocatalyst for the regioselective synthesis of N-alkyl purine, pyrimidine and related N-heterocycles via presilylated method
Behrouz, Somayeh,Soltani Rad, Mohammad Navid,Piltan, Mohammad Amin
, p. 113 - 124 (2019/07/30)
Abstract: The presilylation of purine and pyrimidine nucleobases as well as other related N-heterocycles with HMDS utilizing chitosan–silica sulfate nanohybrid (CSSNH) is described. CSSNH is proved to be a useful, highly efficient and eco-friendly heterogeneous nanohybrid catalyst for silylation of nucleobases. The presilylated nucleobases then underwent the reaction with different sources of carbon electrophiles to afford the desired N-alkyl-substituted derivatives in good-to-excellent yields. CSSNH exhibits several advantageous involving ease of handling and preparation, low cost, reusability and environmental benignity. These unique properties render the CSSNH to be an ideal candidate for use in green industrial processes. Graphic abstract: [Figure not available: see fulltext.].
One-pot protocol for N-alkylation of purine, pyrimidine and azole derivatives via alcohols using Ph3P/I2: simple route for carboacyclic nucleoside synthesis
Soltani Rad, Mohammad Navid,Soleimani, Faezeh
supporting information, p. 4947 - 4953 (2016/07/19)
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.
Regio- and enantioselective N-allylations of imidazole, benzimidazole, and purine heterocycles catalyzed by single-component metallacyclic iridium complexes
Stanley, Levi M.,Hartwig, John F.
supporting information; experimental part, p. 8971 - 8983 (2009/12/04)
Highly regio- and enantioselective iridium-catalyzed N-allylations of benzimidazoles, imidazoles, and purines have been developed. N-Allylated benzimidazoles and imidazoles were isolated in high yields (up to 97%) with high branched-to-linear selectivity
