Characteristic features of interaction between (5-methyl-1,3-thiazolidin-2-ylidene) ketones and tosyl azide
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Characteristic features of interaction between (5-methyl-1,3-thiazolidin-2-ylidene) ketones and tosyl azide Mariia B. Litvinchuk1*, Anton V. Bentya1, Lesya N. Saliyeva2, Eduard B. Rusanov1, Mykhailo V. Vovk1 1
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094, Ukraine; e-mail: [email protected] 2 Lesya Ukrainka Eastern European National University, 13 Voli Ave., Lutsk 43025, Ukraine; e-mail: [email protected]
Submitted May 8, 2020 Accepted June 7, 2020
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(9), 1230–1233
(5-Methyl-1,3-thiazolidin-2-ylidene) ketones, depending on the substituent in the ylidene part of the molecule, interact with tosyl azide to form (5,6-dihydro[1,3]thiazolo[3,2-c][1,2,3]triazol-3-yl) ketones and N-[(5,6-dihydro[1,3]thiazolo[3,2-c][1,2,3]triazol-3-yl)alkylidene]tosylamides. Keywords: 5,6-dihydro[1,3]thiazolo[3,2-c][1,2,3]triazoles, 1,3-thiazolidin-2-ylidene ketones, tosyl azide.
p-Toluenesulfonyl azide (tosyl azide, TsN3) as an available reagent is widely used in synthetic practice. The scope of its preparative application is accounted both to its ability to act as a source of diazo group in the reaction of diazo transfer with methylene active compounds,1–5 and to form various derivatives of 1,2,3-triazole due to the interaction with substrates of the enamine type.6–9 Moreover, the scope of use of tosyl azide includes the selective catalytic amidation of aromatic, α,β-unsaturated carbonyl10 and indole11 compounds, as well as the efficient synthesis of tosylamidines.12,13 A number of interesting works on the use of tosyl azide in transition metal catalyzed synthesis of condensed systems of 1,2,3-triazolopyrimidines,14 1,2,3-triazolopyridoindoles,15 and tosylaminoquinolines16 should be noted. Thiazolo[3,2-c][1,2,3]triazoles have become the subject of our interest due to their synthetic value17–20 and biological attractiveness.21 Usually they are obtained by the oxidative cyclization of 2-acyl-1,3-thiazolehydrazones.18–20 There is also one report22 on the synthesis of this type of compounds by [3+2] cycloaddition of tosyl azide to cyclic 2-aroyl-S,N-ketene acetals. So it seemed reasonable to study in a similar process the recently synthesized by us 0009-3122/20/56(9)-1230©2020 Springer Science+Business Media, LLC
(5-methyl-1,3-thiazolidin-2-ylidene) ketones 1а–с, the enamine fragment of which has already been successfully utilized in cyclocondensations with activated alkenes and alkynes,23 and also 1-chlorobenzyl isocyanates.24 During the study of the interaction of tosyl azide with compounds 1а–c, it was revealed that the reaction with methyl and ethyl ketones 1а,b proceeds in dioxane solution at room temperature for 10 h and, according to the 1 Н NMR spectrum and mass spectra, leads to the formation of a mixture of three types of 1,3-thiazolidine triazoloannulation products in the following ratios: compounds 2а:3a:4 = 68:25:7, compounds 2b:3b:4 = 79:8:13. However, in the case of phenyl ketone 1c, this in
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