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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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.
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cited_by cdi_FETCH-LOGICAL-c277t-a67a5b8aad241de23023abaab878073ee350b0861fea29e38ca82a9d44b1f75d3
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container_end_page 3631
container_issue 23
container_start_page 3622
container_title Synthesis (Stuttgart)
container_volume 52
creator Fedotov, Victor V.
Ulomsky, Evgeny N.
Savateev, Konstantin V.
Mukhin, Evgeny M.
Gazizov, Denis A.
Gorbunov, Evgeny B.
Rusinov, Vladimir L.
description 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.
doi_str_mv 10.1055/s-0040-1707228
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title A PASE Approach to the Synthesis of Benzimidazopurines as Polycondensed Purine Derivatives
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