TY - JOUR
T1 - 2-(1,3,5-Dithiazinan-5-yl)ethanol heterocycles, structure and reactivity
AU - Gálvez-Ruiz, Juan Carlos
AU - Jaen-Gaspar, Javier C.
AU - Castellanos-Arzola, Indira G.
AU - Contreras, Rosalinda
AU - Flores-Parra, Angelina
PY - 2004/10/1
Y1 - 2004/10/1
N2 - 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 NEt 3 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.
AB - 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 NEt 3 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.
M3 - Article
SP - 2269
EP - 2285
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
ER -