New Synthesis of Thiophene-3,4-Imido Amino Acid Esters and: Investigation of Their Electrochemical Behaviors
Letters in Organic Chemistry, 2026 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Basım Tarihi: 2026
- Doi Numarası: 10.2174/0115701786431043251202193750
- Dergi Adı: Letters in Organic Chemistry
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core
- Anahtar Kelimeler: 3,4-disubstitued thiophene, 3,4-imido amino acid, amino acid, electrochemistry, imid, redox properties, Thiophene
- Eskişehir Osmangazi Üniversitesi Adresli: Evet
Özet
Benzotriazole-mediated thiophene-3,4-imido-L-amino acid esters (L-phenylalanine methyl ester, L-tyrosine methyl ester, and L-aspartic acid methyl ester) were synthesised from thiophene-3,4-dicarboxylic acid via thiophene-3,4-anhydride to model the reactions of aromatic, phenolic, and polar amino acids, respectively. In synthetic studies, L-amino acids were first reacted with thiophene-3,4-anhydride to produce thiophene intermediates with a carboxylic acid group in the 3-position and an amide group in the 4-position. These intermediates' carboxylic acid functions were then activated using the N-acylbenzotriazole method. This resulted in an in situ cyclisation reaction that was distinct from conventional N-acylbenzotriazole reactions. This reaction formed the target products -thiophene-3,4-imido-L-amino acid esters- in good yields. The electrochemical properties of the thiophene-3,4-imido amino acid ester derivatives, which are free from the 2,5-position of thiophene, were investigated. The structures of thiophene-3,4-imido amino acid esters were examined using 1H and 13C NMR spectroscopy.