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Novel 1,5,3-dithiazepanes: three-component synthesis, stereochemistry, and fungicidal activity |
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| Authors: | V R Akhmetova N N Murzakova T V Tyumkina G R Khabibullina I S Bushmarinov L F Korzhova N F Galimzyanova |
| Institution: | 1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075, Ufa, Russian Federation 2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation 3. Bashkir Republic Research Center of Ecology, 147 prosp. Oktyabrya, 450075, Ufa, Russian Federation 4. Institute of Biology, Ufa Research Center of the Russian Academy of Sciences, 69 prosp. Oktyabrya, 450054, Ufa, Russian Federation |
| 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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