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Thionyl Chloride-Mediated Synthesis of Erlenmeyer Azlactones from N-Acylated α-Amino Acids
Hajar Aledwan1, Guy Zimmermann1, Arjun Veliyil Prakash1
1Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel.
Abstract:
A thionyl chloride-mediated synthesis of Erlenmeyer azlactones from N-acylated α-amino acids is described. The method relies on in situ activation of the carboxylic acid with SOCl2 followed by base-promoted intramolecular cyclization, enabling direct access to diverse azlactones in moderate to good yields. Under microwave irradiation, the transformation proceeds efficiently and tolerates a range of N-acylated phenylalanine derivatives as well as selected aliphatic and aromatic amino acids. Control experiments highlight the unique role of thionyl chloride in promoting the cyclization. This protocol provides a straightforward route to azlactone scaffolds from readily available amino acid precursors.
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