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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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