Synthesis of new organochalcogen (Se or Te) based multifunctional pyrimidine derivatives: X-ray structure determination of 2,4- bis(arylchalcogenyl)pyrimidine and 2-chloro-4,6-bis(arylchalcogenyl)pyrimidine compounds

Abstract

A new class of multinucleate pyrimidine chalcogen (Se/Te) derivatives, i.e. 2,4-bis(arylchalcogenyl)pyrimidine and 2-chloro-4,6-bis(arylchalcogenyl) pyrimidine compounds, has been synthesized for the first time by the nucleophilic substitution of chlorine at the C-2 and C-4 positions of 2,4-dichloropyrimidine and at the C-4 and C-6 positions of 2,4,6- trichloropyrimidine with a variety of chalcogen bearing aryl anions ArE - (Ar = phenyl, 1-naphthyl, p-tolyl). All the newly prepared pyrimidyl chalcogen compounds have been thoroughly characterized with the help of various spectroscopic techniques, viz, NMR (1H, 13C, 77Se), FT-IR and mass spectrometry (in representative cases). The crystal structures of 2,4-bis(naphthalen-1-ylselanyl)pyrimidine (1c), 2,4-bis(phenyltelluryl)pyrimidine (1d), 2-chloro-4,6-bis(phenylselanyl) pyrimidine (2a) and 4,6-bis(p-tolylselanyl)-2-chloropyrimidine (2b) were confirmed by X-ray crystallographic analysis. © 2014 Elsevier Ltd. All rights reserved.