Abstract
Three-component heterocyclization of hydrazine with formaldehyde and ethane-1,2-dithiol gave previously unknown 3,3′-bi(1,5,3-dithiazepane). Its stereochemistry was determined by X-ray diffraction. The reaction with higher aliphatic aldehydes RCHO (R = Me, Et, Prn, and Bun) yielded 2,4-dialkyl-3-alkylideneamino-1,5,3-dithiazepanes. The stereochemistry of the latter was determined by 1H and 13C NMR spectroscopy and confirmed by quantum chemical calculations. Heterocyclizations of phenylhydrazine and benzylhydrazine with ethane-1,2-dithiol gave 3-amino-1,5,3-dithiazepanes only with CH2O and MeCHO as the aldehyde component. 3,3′-Bi(1,5,3-dithiazepane) and its N-adduct with MeI were found to exhibit fungicidal activity against microscopic fungi.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2123–2131, November, 2012.
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Akhmetova, V.R., Murzakova, N.N., Tyumkina, T.V. et al. Novel 1,5,3-dithiazepanes: three-component synthesis, stereochemistry, and fungicidal activity. Russ Chem Bull 61, 2140–2148 (2012). https://doi.org/10.1007/s11172-012-0301-5
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DOI: https://doi.org/10.1007/s11172-012-0301-5