Abstract
N,N′-Bis(hydroxymethyl)thiourea reacted with propane-1,3-diamine at a molar ratio of 2 : 1 to give 5,5′-propane-1,3-diylbis(1,3,5-triazinane-2-thione), whereas 1,3,5,7,11,13,15,17-octaazatricyclo[15.3.1.17,11]-docosane-4,14-dithione was obtained in the reaction with equimolar amounts of the reactants. Tricyclic product was also formed in the three-component condensation of thiourea with formaldehyde and propane-1,3-diamine at a ratio of 1 : 3 : 1. The reactions of N,N′-bis(hydroxymethyl)thiourea with ethane-1,2-diamine (2 : 1) and of thiourea with formaldehyde and butane-1,4-diamine (1 : 2 : 1) afforded 5,5′-(ethane-1,2-diyl)bis(1,3,5-triazinane-2-thione) and 5,5′-(butane-1,4-diyl)bis(1,3,5-triazinane-2-thione), respectively.
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Original Russian Text © F. Hamoud, S.M. Ramsh, V.S. Fundamenskii, V.V. Gurzhii, M.A. Brusina, N.G. Arkhipova, P.A. Sedunova, N.L. Medvedskii, E.S. Khrabrova, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 1, pp. 127–132.
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Hamoud, F., Ramsh, S.M., Fundamenskii, V.S. et al. Reaction of thiourea with formaldehyde and simplest aliphatic diamines. Russ J Org Chem 52, 121–126 (2016). https://doi.org/10.1134/S1070428016010231
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DOI: https://doi.org/10.1134/S1070428016010231