35186-33-5Relevant academic research and scientific papers
Spectrometric and Chemical Studies of 5-Acyl- and 5-Nitroso-2-(N,N-disubstituted Amino)thiazoles
Birkinshaw, Timothy N.,Meakins, G. Denis,Plackett, Simon J.
, p. 2209 - 2212 (2007/10/02)
The conformational preferences of 2-(N,N-disubstituted amino)thiazoles having a 4-substituent (R1) and a 5-acyl group (R2CO) have been established by i.r. spectrometry and a crystallographic examination.In solution the compounds with R2=aryl and R1=Me or aryl exist predominantly or entirely in the carbonyl O,S-anti arrengement; for those with R1=aryl and R2=Me the syn rotamer is the main form but a small amount (ca. 15percent) of the anti rotamer is present.Nitrosation of 4-aryl-2-dimethylaminothiazoles gives 5-nitoso derivatives, and these are probably the first authentic nitrosothiazoles.The barrier to rotation of the dimethylamino group is unexpectedly high (ΔG(excit.)298=69 kJ mol-1), exceeding even that of the 5-trifluoroacetyl analogous.
