A PASE Approach to the Synthesis of Benzimidazopurines as Polycondensed Purine Derivatives

Abstract A highly efficient PASE approach to a new class of polycyclic purine derivatives has been proposed. The strategy includes a consecutive reduction, auto-aromatization, and heterocyclization of the initial nitrobenzimidazopyrimidines obtained by a three-component condensation. It was shown th...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2020-12, Vol.52 (23), p.3622-3631
Main Authors: Fedotov, Victor V., Ulomsky, Evgeny N., Savateev, Konstantin V., Mukhin, Evgeny M., Gazizov, Denis A., Gorbunov, Evgeny B., Rusinov, Vladimir L.
Format: Article
Language:English
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Summary:Abstract A highly efficient PASE approach to a new class of polycyclic purine derivatives has been proposed. The strategy includes a consecutive reduction, auto-aromatization, and heterocyclization of the initial nitrobenzimidazopyrimidines obtained by a three-component condensation. It was shown that reduction of nitrobenzimidazopyrimidines by metals in acidic media was more efficient than heterogeneous hydro­genation. Novel derivatives of benz[4,5]imidazo[1,2- a ]purines were obtained­ in good yields and the proposed structure was confirmed by X-ray crystal structure analysis. The obtained convergent benzimidazopurines combine two relevant medicinal chemistry scaffolds – benz­imidazole and purine.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0040-1707228