An efficient synthesis of novel 2-amino-4- aryl-6-ferrocenyl pyrimidines

The discovery of ferrocene in 1951 sparked off a truly remarkable interdisciplinary research activity. Since then ferrocene and its derivatives have been immensely exploited for their potential applications in diverse fields such as homogeneous catalysis, organic synthesis, supramolecular chemistry, biosensors, medicinal chemistry and materials science. It is now well established that ferrocene functionalized organic compounds often exhibit unexpected biological activity owing to different membrane permeation properties and anomalous metabolism. Owing to the resemblance of ferrocene to benzene, the substitution of the latter by the former in a biologically active compound is expected to induce dramatic change in properties like charge distribution, solubility and hydrophobicity. The stability and non toxicity of ferrocenyl group in aqueous and aerobic media has made it an ideal candidate for use in drug designing. With this background, the incorporation of one or more ferrocene units into a heterocyclic ring has become a relevant strategy of research in the communities of both organometallic chemists and biologists in expanding the potential applications of heterocyclic compounds. The past few years have seen a tremendous boost in ferrocene functionalized heterocyclic chemistry, as an avalanche of research activity has been directed towards this end. Pyrimidine is a fundamental part of nucleic acids and has been associated with a number of biological activities. Aminopyrimidine constitutes one of the important classes of pyrimidines and its various derivatives have displayed interesting antibacterial, antitumor and HIV-I inhibiting activity. Also, the pyrimidine and aminopyrimidine structures are frequently occurring motifs in commercially available drugs such as anti-atherosclerotic aronixil, antihistaminic thonzylamine, anti-anxiolytic buspirone, anti-psoriatic enazadrem, and other medicinally relevant compounds. A survey of literature reveals that no synthesis of ferrocene functionalized aminopyrimidines has been reported though a number of reports have been published which describe the synthesis of various ferrocene functionalized heterocycles. In this communication, is reported the synthesis of some novel 2-amino-4-aryl-6-ferrocenyl pyrimidines by the base induced condensation of various 3-aryl-1ferrocenyl-2-propen-1-ones (ferrocenyl chalcones) with guanidine hydrochloride.