Synthesis and Reaction of 2-Mercapto-3-Arylpropanoic Acids |
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Authors: | Nazariy T Pokhodylo Vasyl S Matiychuk Mykola D Obushak |
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Institution: | Department of Organic Chemistry, Ivan Franko National University of Lviv , Lviv , Ukraine |
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Abstract: | Abstract Two synthetic pathways for the preparation of 2-mercapto-3-arylpropanoic acids were developed. First, by the reaction of arenediazonium bromides with acrylic esters in the presence of CuBr, alkyl (2-bromo-3-aryl)propanoates were formed. Their cyclization with thiourea produced 5-(R-benzyl)-2-imino-4-thiazolidinones, which yielded 3-aryl-2-mercaptopropanoic acids by alkaline hydrolysis. Second, direct Meerwein arylation of acrylates in the presence of S-nucleophile (NaSH) allowed isolation of 3-phenyl-2-mercaptopropanoic acid in 8% yield. Such acids were used for cyclization with cyanoguanidine and phenyl isothiocyanate yielding 1-5-(R-benzyl)-4-oxo-1,3-thiazolidin-2-ylidene]guanidines and new 5-(R-benzyl)-3-phenyl-2-thioxo-1,3-thiazolidin-4-one (rhodanine) derivatives correspondingly. |
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Keywords: | Mercapto acids thiazolidinone derivatives arylation Meerwein reaction cyclization cyanoguanidine |
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