Kaye, Perry T.; Meakins, G. Denis; Willbe, Charles; Williams, Peter R. published the article 《An infrared study of rotational isomerism in thiazole-2-carboxylates》. Keywords: thiazolecarboxylate IR rotational isomerism; Hantzsch thiourea bromoacetone; bromomethylthiazolecarboxylate ethyl methyl; methylthiazolecarboxylate bromo ethyl methyl; carboxylate thiazole IR rotational isomerism.They researched the compound: 5-Bromo-4-methyl-thiazol-2-ylamine hydrobromide( cas:79247-77-1 ).Category: amides-buliding-blocks. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:79247-77-1) here.
Twenty-five alkyl thiazole-2-carboxylates with a range of 4- and 5-substituents were prepared through the Hantzsch synthesis. E.g., cyclocondensation reaction of (H2N)2CS with MeCOCH2Br followed by bromination, oxidation, and alkylation gave the thiazole esters I (R = Me, Et). Solutions of these esters show well resolved doublets in the carbonyl IR spectra, due to rotational isomers. The higher wave number components were assigned to the more polar carbonyl O,S-anti-s-trans rotamers and those at lower wave number to the O,S-syn-s-trans forms. Small, but systematic, differences between the Me esters were noted.
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Reference:
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