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Cyclothiomethylation of primary amines with formaldehyde and aromatic dithiols – an effective method for the synthesis of cyclophanes

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Chemistry of Heterocyclic Compounds Aims and scope

An effective method has been developed for the synthesis of S,N- and S,N,O-containing cyclophanes by cyclothiomethylation reaction of primary amines with formaldehyde and aromatic dithiols. Benzene-1,2-dithiols were used in [1+2+1] cyclocondensation reaction that gave N-substituted 1,5,3-benzodithiazepines, while benzene-1,4-dithiol and 4,4'-dimercaptodiphenyl oxide participated in a [3+6+3] cyclocondensation reaction leading to cyclophanes.

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Acknowledgement

This work received financial support from the Grants Council of the President of the Russian Federation (grant NSh-5240.2018.3) and funding from the Project part of the State assignment (AAAA-A17-117012610060-7 and AAAAA17-117011910027-0)

The structural characterization of the compounds was performed at the Collective Use Center “Agidel” of the Institute of Petrochemistry and Catalysis of the Russian Academy of Sciences. Mass spectra of compounds 3с,d, 4e,f, 6, and 8a,b were recorded at the Collective Use Center “Chemistry” of the Ufa Institute of Chemistry, Russian Academy of Sciences.

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Oktyabrya Ave, Ufa, 450075, Russia

    Guzel R. Khabibullina, Ekaterina S. Fedotova, Tatyana V. Tyumkina, Askhat G. Ibragimov & Usein M. Dzhemilev

  2. Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave, Ufa, 450054, Russia

    Marat F. Abdullin

Authors
  1. Guzel R. Khabibullina
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  2. Ekaterina S. Fedotova
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  3. Tatyana V. Tyumkina
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  4. Marat F. Abdullin
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  5. Askhat G. Ibragimov
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  6. Usein M. Dzhemilev
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Correspondence to Guzel R. Khabibullina.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(7), 744–750

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Khabibullina, G.R., Fedotova, E.S., Tyumkina, T.V. et al. Cyclothiomethylation of primary amines with formaldehyde and aromatic dithiols – an effective method for the synthesis of cyclophanes. Chem Heterocycl Comp 54, 744–750 (2018). https://doi.org/10.1007/s10593-018-2341-8

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  • DOI: https://doi.org/10.1007/s10593-018-2341-8

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