Synthesis of New Family of Thiazoline and Thiazole Esters and Investigation of their Thermal Properties

A new family of thiazoline and thiazole esters has been synthesized and their thermal properties are presented and discussed. Thiazoline esters were obtained by cyclization reaction from 4-substituted benzenenitrile and amino acid L-cysteine followed by esterification reaction with selected alcohols...

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Bibliographic Details
Published in:Journal of the Brazilian Chemical Society 2014-08, Vol.25 (8), p.1493-1503
Main Authors: Schneider, Juliana M. F. M., Sales, Eric S., Livotto, Paolo R., Schneider, Paulo H., Merlo, Aloir A.
Format: Article
Language:English
Subjects:
CHEMISTRY, MULTIDISCIPLINARY
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Summary:A new family of thiazoline and thiazole esters has been synthesized and their thermal properties are presented and discussed. Thiazoline esters were obtained by cyclization reaction from 4-substituted benzenenitrile and amino acid L-cysteine followed by esterification reaction with selected alcohols and phenol. Subsequent oxidation step to transform thiazoline esters into thiazole esters was applied mediated by BrCCl3/DBU. The final thiazoline and thiazole esters are composed by terminal flexible hydrogenated alkyl chain from one side and to the other side by terminal segments of flexible alkyl chains (hydrogenated chain), (perfluoralkyl)alkyl chains (semifluorinated alkane) p-alkoxyphenyl chains. Some liquid crystals compounds for thiazoline and thiazole esters showed to be relevant. One of the thiazoline esters display a monotropic smectic A (SmA) mesophase while some thiazole esters show stable SmA mesophase. As expected semifluorinated alkane chain induce the formation of orthogonal mesophase by means of segregation effect.
ISSN:0103-5053
1678-4790
DOI:10.5935/0103-5053.20140132