58350-43-9Relevant articles and documents
Structural Features and Crystallographic Examination of 5-Acetyl- and 5-Trifluoroacetyl-2-(N,N-disubtituted amino)thiazoles
Caldwell, Jennifer M.,Meakins, G. Denis,Jones, Richard H.,Kidd, Timothy R.,Prout, Keith
, p. 2305 - 2310 (2007/10/02)
5-Acetyl-2-(N,N-disubstituted amino)thiazoles, unsubstituted or with Me, But, or Ph groups at position 4, have been prepared by unambiguous methods and examined spectrometrically; crystallographic studies have been carried out on four of the compounds and a related 4-aryl-5-trifluoroacetylthiazole.In solution the 4-H, 4-But, and 4-Ar compounds exist predominantly in one conformation but with the 4-Me compounds, two forms (carbonyl O,S-syn or anti, related by rotation of the 5-acetyl group) of approximately equal stability are present.The X-ray work establishes that for 5-acetylthiazoles, as solids, the 4-H and 4-Ph derivatives have the carbonyl O,S-syn stereochemistry whereas the 4-Me and 4-But derivatives have the anti arrangement; in contrast with the 5-acetyl-4-phenyl compound the 4-aryl-5-trifluoroacetylthiazole adopts the anti arrangement.These findings validate a correlation, for solutions, between the stereochemistry of the rotational isomers and the positions of their i.r.CO bands.The results confirm the operation of a strong mesomeric interaction between the 2-NR2 and 5-CH3(CF3)CO groups.
