Synthesis of 1,3,4-thiadiazol-2-ylacetic acid derivatives |
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Authors: | Toshinori Saito Norio Saheki Minoru Hatanaka Toshiyasu Ishimaru |
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Abstract: | 1,3,4-Thiadiazol-2-ylacetic acids 4 were prepared by lithiation of 2-methyl-1,3,4-thiadiazoles 1 , followed by treatment with carbon dioxide. Diethyl 1,3,4-thiadiazol-2-ylmalonates 6 were prepared by nucleophilic displacement reaction of the corresponding bromides 5 with diethyl malonate. Introduction of the amino group at the a-position of 4 or 6 was carried out via oximation or bromination to give the amino ester 9 or 4 . Attempts to prepare DL-α-amino-1,3,4-thiadiazol-2-ylacetic acids from 9 or 4 were unsuccessful because the amino acids were decarboxylated too rapidly to be isolated in the free form. |
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