3020-73-3Relevant academic research and scientific papers
N,N-Disubstituted 2-Aminothiazole-5-carbaldehydes: Preparation and Investigation of Structural Features
Gillon, David W.,Forrest, Ian J.,Meakins, G. Denis,Tirel, Malcolm D.,Wallis, John D.
, p. 341 - 348 (2007/10/02)
Methods of preparing N,N-disubstituted 2-aminothiazoles have been investigated. 4-Substituted N,N-dimethyl-, N-benzyl-N-methyl-, and N-methyl-N-phenyl-amines were prepared and converted by Vilsmeier formylation into 2-amino-5-carbaldehydes which were examined by i.r. and 1H n.m.r. spectrometry.The aldehyde group adopts the carbonyl O,S-syn-conformation.With the N,N-dimethyl and N-benzyl-N-methyl compounds the barrier to rotation of the amine group (ΔG(excit.)) is 50-55 kJ mol-1 and is insensitive to the nature of the 4-substituent.The amine group of the N-methyl-N-phenyl compounds has a marked preference for one orientation.This was shown by a crystallographic study of 4-t-butyl-2-(N-methyl-N-phenylamino)thiazole-5-carbaldehyde to have the phenyl group directed towards the sulphur atom of the thiazole ring.
Carbonyl Diisothiocyanate
Bunnenberg, Rolf,Jochims, Johannes C.
, p. 2075 - 2086 (2007/10/02)
A cheap synthesis of carbonyl diisothiocyanate (1) from ammonium thiocyanate and phosgene is reported.As a strong electrophil 1 forms the 6-substituted 2-thioxo-1,3,5-thiadiazine-4-ones 4 - 7 with water, alcohols, hydrogensulfide, mercaptanes, ammonia, and amines.With excess nucleophil the ring of the heterocycles is opened.Addition to the NCS group or substitution of this group leads to compounds 9, 11, 12, 14, and 15.Thermally the thiadiazinones 7e, h rearrange to the dithioisocyanuric acids 10a, b.Some physical properties ( e. g. pK values, hindered rotations) of the compounds are described.
