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Thiomethylation of heteroaromatic amines

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Abstract

Thiomethylation of heteroaromatic amines with formaldehyde-hydrogen sulfide gave linear and cyclic heteroatom compounds: N,N′-[methylenebis(sulfanediylmethylene)]bishetarenamines and 5-hetaryl-1,3,5-dithiazinanes. N,N′-[Methylenebis(sulfanediylmethylene)]bishetarenamines were found to undergo transformation into 5-hetaryl-1,3,5-dithiazinanes by the action of CH2O-H2S. Transamination of 5-methyl-1Hpyrazol-3-amine, 6-nitro-1,3-benzothiazol-2-amine, and 5-bromopyridin-2-amine with 5-methyl-1,3,5-dithiazinane selectively afforded the corresponding 5-hetaryl-1,3,5-dithiazinanes.

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Authors and Affiliations

  1. Institute of Petroleum Chemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, Ufa, 450075, Bashkortostan, Russia

    V. R. Akhmetova, Z. T. Niatshina & A. G. Ibragimov

  2. Nesmeyanov Institute of Organometallic Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow, 119991, Russia

    Z. A. Starikova

  3. Bashkir Republican Research Ecological Center, pr. Oktyabrya 147, Ufa, 450075, Bashkortostan, Russia

    L. F. Korzhova

Authors
  1. V. R. Akhmetova
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  2. Z. T. Niatshina
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  3. Z. A. Starikova
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  4. L. F. Korzhova
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  5. A. G. Ibragimov
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Correspondence to V. R. Akhmetova.

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Original Russian Text © V.R. Akhmetova, Z.T. Niatshina, Z.A. Starikova, L.F. Korzhova, A.G. Ibragimov, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 6, pp. 903–910.

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Akhmetova, V.R., Niatshina, Z.T., Starikova, Z.A. et al. Thiomethylation of heteroaromatic amines. Russ J Org Chem 47, 920–927 (2011). https://doi.org/10.1134/S1070428011060157

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  • DOI: https://doi.org/10.1134/S1070428011060157

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