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Lewis acid catalyzed condensation of 2-aminohetarene N-oxides with N,N-dimethylformamide dimethyl acetal

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Chemistry of Heterocyclic Compounds Aims and scope

A method for the introduction of the N,N-dimethylformamidine protective group in a series of six-membered 2-aminohetarene N-oxides was developed. It was shown that 2-amino derivatives of N-oxides of various six-membered heterocycles (pyridines, pyrimidines, pyrazines, tetrazines) successfully enter the reaction. The stability of the N,N-dimethylformamidine protecting group in 2-aminohetarene N-oxides was found to depend on the type of reaction medium.

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This work was carried out with the financial support of the Russian Foundation for Basic Research and the Moscow Government within the framework of the scientific project No. 21-33-70056.

X-ray structural studies and quantum-chemical calculations were carried out with the support of the Ministry of Science and Higher Education of the Russian Federation using the scientific equipment of the Center for Molecular Structure Studies of A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave, Moscow, 119991, Russia

    Sergey А. Karalash, Dmitry M. Bystrov & Leonid L. Fershtat

  2. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Sergey А. Karalash

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St, Moscow, 119991, Russia

    Ivan V. Ananyev

Authors
  1. Sergey А. Karalash
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  2. Dmitry M. Bystrov
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  3. Ivan V. Ananyev
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  4. Leonid L. Fershtat
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Corresponding author

Correspondence to Leonid L. Fershtat.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(11), 1130–1136

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Karalash, S.А., Bystrov, D.M., Ananyev, I.V. et al. Lewis acid catalyzed condensation of 2-aminohetarene N-oxides with N,N-dimethylformamide dimethyl acetal. Chem Heterocycl Comp 57, 1130–1136 (2021). https://doi.org/10.1007/s10593-021-03031-0

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