Application of TLC and HPLC/MS methods for the optimize of the conditions for the synthesis of 10-aminobenzo[4,5]imidazo[1,2-A]pyrimidines
Abstract
The modern rational design of polyfunctional (according to practical use) heterocyclic compounds requires high efficiency due to the need simultaneously increase the molecular complexity and minimize the number of steps in synthetic procedures. These problems become even more important in the construction of various polyazaheterocyclic structures, including those containing an imidazole fragment. Therefore, the problems associated with the search for new selective synthetic approaches to the construction of heterocyclic systems based on imidazole, the study of the mechanisms of their formation, reactivity and further directed functionalization, the choice of available reagents for their synthesis using chromatographic methods are important.
Therefore, 1,2-diaminoimidazoles with dual reactivity are promising compounds. The presence in this molecule of four (1,2-diamino-4-R-imidazole) or three (1,2-diaminobenzimidazole, 1,2-diamino-4-R-5-R1-imidazole) of non-equivalent nucleophilic centres provides alternative possibilities in the direction of reactions with dielectrophiles, which, due to the selection of certain conditions and catalysts, opens up wide possibilities for obtaining new five-, six-, and seven-membered annelated and linearly bonded nitrogen-containing heterocyclic compounds, which are also promising for use as additives in the processes of electrochemical copper plating [1-2].
In this study, we proposed a new method for obtaining imidazo[1,2-A]pyrimidines formed during the interaction of 1,2-diaminobenzimidazole with dimethylacetylenedicarboxylate. Using HPLC-MS and thin-layer chromatography (TLC), the optimal conditions for this reaction were studied and selected.
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