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Issue 34, 2020
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Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity

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Abstract

We discovered a reaction of nitroalkanes with 2-hydrazinylquinolines, 2-hydrazinylpyridines and bis-2,4-dihydrazinylpyrimidines in polyphosphoric acid (PPA) affording 1,2,4-triazolo[4,3-a]quinolines, 1,2,4-triazolo[4,3-a]pyridines and bis[1,2,4]triazolo[4,3-a:4′,3′-c]pyrimidines, respectively. The reaction expands the scope of heterocyclic annulations involving phosphorylated nitronates, believed to be the electrophilic intermediates formed from nitroalkanes in PPA. Several of the synthesized triazoles showed promising anticancer activity by inducing differentiation in neuroblastoma cancer cells. Due to the urgent need for novel differentiation agents for neuroblastoma therapy, this finding warrants further evaluation of this class of compounds against neuroblastoma.

Graphical abstract: Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity

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Article information


Submitted
15 May 2020
Accepted
13 Aug 2020
First published
13 Aug 2020

Org. Biomol. Chem., 2020,18, 6651-6664
Article type
Paper

Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity

N. A. Aksenov, A. V. Aksenov, N. K. Kirilov, N. A. Arutiunov, D. A. Aksenov, V. Maslivetc, Z. Zhao, L. Du, M. Rubin and A. Kornienko, Org. Biomol. Chem., 2020, 18, 6651
DOI: 10.1039/D0OB01007C

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