85656-33-3Relevant academic research and scientific papers
2-(N,N-Disubstituted Amino)thiazoles with Electron-withdrawing Groups at Position 5: Prepaeation and Investigation on Structural Features
Birkinshaw, Timothy N.,Gillon, David W.,Harkin, Shaun A.,Meakins, G. Denis,Tirel, Malkom D.
, p. 147 - 153 (2007/10/02)
A convenient procedure for preparing N-mono- and NN-di-substituted cyanamides from cyanogen bromide has been developed.N,N-Disubstituted thioureas, obtained from the cyanamides, were condensed with α-bromo-α-cyanoketones to give 5-cyano-2-(N,N-disubstituted amino)thiazoles and with α-bromo-ketones to give 2-(N,N-disubstituted amino)thiazoles.Substitution in the latter products afforded 5-trifluoroacetyl- and 5-nitro-2-(N,N-disubstituted amino)thiazoles; nitration is greatly facilitated by the presence of a 4-aryl group.The average values of the barriers of rotation of the barriers to rotation of the 2-NR2 groups (ΔG298) in the 5-substituted thiazoles were established by variable temperature 1H n.m.r. spectrometry to be 57.4 kJ mol -1 (5-NO2), 56.2 (5-COCF3), and 51.5 (5-CN).I.r. examination showed that the 5-trifluoroacetyl compounds adopt one rotational form preferentially; this is probably the carbonyl O,S-syn-conformation.
N,N-Disubstituted 2-Aminothiazole-5-carboxylates: Preparation and Rotation of Functional Groups
Kaye, Perry T.,Meakins, G. Denis,Smith, Anthony K.,Tirel, Malcolm D.
, p. 1677 - 1680 (2007/10/02)
A series of new alkyl N,N-disubstituted 2-aminothiazole-5-carboxylates was prepared by condensing α-bromo-β-oxo-esters with N,N-disubstituted thioureas.The products exhibit i.r. carbonyl doublets, the higher and lower wavenumber components arising from th
