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Paper | Regular issue | Vol 63, No. 10, 2004, pp.2269-2285
Published online, 27th August, 2004
DOI: 10.3987/COM-04-10151
2-(1,3,5-Dithiazinan-5-yl)ethanol Heterocycles, Structure and Reactivity

Juan Carlos Gálvez-Ruiz, Javier C. Jean-Gaspar, Indira G. Castellanos-Arzola, Rosalinda Contreras, and Angelina Flores-Parra*

*Chemistry Department , Centro de Investigación y de Estudios Avanzados del I.P.N., A.P. 14-740, C.P. 07000 México, D.F., Mexico


Treatment of 2-(1,3,5-dithiazinan-5-yl)ethanol (1), 2-(1,3,5-dithiazinan-5-yl)-1-phenylethanol (2), 2-(1,3,5-dithiazinan-5-yl)-1-methylethanol (3) and 2-(1,3,5-dithiazinan-5-yl)-2-methyl-1-phenylethanol (4) with TsCl and NEt3 in CH2Cl2 afforded the corresponding 3-tosyl-1,3-oxazolidine derivatives (5-8), whereas tosylation of 1-4 in the presence of NHMe3Cl gave the corresponding O-tosyl-2-(1,3,5-dithiazinan-5-yl)ethanol derivatives (11-14). The direct preparation of 5 and 7 from formaldehyde and N-tosylethanolamine (9) or N-tosyl-2-propanolamine was not successful. Reactions of 1 or 3 with benzylamine furnish 1,3,5-tribenzyl-1,3,5-triazinane. Heating of 1 and 2 affords the corresponding 1,3,5-tri(2-hydroxyethyl)-1,3,5-triazinanes. X-Ray diffraction studies of compounds (1-9 and 11) are reported.