Abstract
The reaction of m-aminophenol with CH2O and H2S (1: 2: 1 ratio) afforded 2, 12-dioxa-4, 14-dithia-6, 16-diazatricyclo[15.3.1.17,11]docosa-1(20), 7(22), 8, 10, 17(21), 18-hexaene in ∼9% yield. Aminophenol o-and p-isomers react with CH2O and H2S (1: 3: 2) to form 2-and 4-[4H-1,3,5-dithiazin-5(6H)-yl]phenols in 86 and 71% yields, respectively. In the crystal structure of the latter, molecules contain dithiazine cycles in the chair conformation with the axial hydroxyphenyl group. Molecular packing represents a combination of molecules forming chains due to the OH...S intermolecular hydrogen bond.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 305–308, February, 2006.
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Akhmetova, V.R., Nadyrgulova, G.R., Khafizova, S.R. et al. Reactions of aminophenols with formaldehyde and hydrogen sulfide. Russ Chem Bull 55, 312–316 (2006). https://doi.org/10.1007/s11172-006-0254-7
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DOI: https://doi.org/10.1007/s11172-006-0254-7