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Cyclothiomethylation of carboxylic acid hydrazides with aldehydes and H2S

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Abstract

The cyclothiomethylation of carboxylic acid hydrazides RCONHNH2 (R = C5H4N, Ph, 2-MeOC6H4, or 4-HOC6H4CH2) with formaldehyde and H2S at 70 °C affords predominantly the corresponding N-(1,3,5-dithiazinan-5-yl)amides, whereas this reaction at 0–−50 °C gives a mixture of the latter compounds with 3-acyl-1,3,4-thiadiazolidines. N-(1,3,5-Dithiazinan-5-yl)-amides were selectively synthesized by the reaction of carboxylic acid hydrazides with formaldehyde and H2S in the presence of BuONa in BuOH.

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075, Ufa, Russian Federation

    V. R. Akhmetova, R. R. Khairullina & T. V. Tyumkina

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    Yu. V. Nelyubina, A. F. Smol’yakov, I. S. Bushmarinov & Z. A. Starikova

  3. Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    M. F. Abdullin

  4. Ufa State Academy of Economy and Service, 145 ul. Chernyshevskogo, 450077, Ufa, Russian Federation

    R. V. Kunakova

Authors
  1. V. R. Akhmetova
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  2. R. R. Khairullina
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  3. T. V. Tyumkina
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  4. Yu. V. Nelyubina
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  5. A. F. Smol’yakov
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  6. I. S. Bushmarinov
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  7. Z. A. Starikova
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  8. M. F. Abdullin
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  9. R. V. Kunakova
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Corresponding author

Correspondence to V. R. Akhmetova.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 416–424, February, 2010.

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Akhmetova, V.R., Khairullina, R.R., Tyumkina, T.V. et al. Cyclothiomethylation of carboxylic acid hydrazides with aldehydes and H2S. Russ Chem Bull 59, 425–433 (2010). https://doi.org/10.1007/s11172-010-0096-1

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  • DOI: https://doi.org/10.1007/s11172-010-0096-1

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