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Convenient synthesis of some novel amino acid coupled triazoles

Department of Chemistry, Faculty of Science, Suez Canal University, Ismailia, Egypt;
(This article belongs to the section C. Bioorganic Chemistry and Natural Products)
Cite this paper as: El Rayes, S. Convenient synthesis of some novel amino acid coupled triazoles. In Proceedings of the 13th Int. Electron. Conf. Synth. Org. Chem., 1-30 November 2009; Sciforum Electronic Conferences Series, 2009, c007:1-7.
Abstract: This study describes a promising one-pot synthesis of [2-(5-benzyl-4-phenyl-4H- [1,2,4]triazol-3-thio)-acetyl]-amino acid methyl esters 6a-h and dipeptides 10a-e were successfully synthesized starting from amino acid esters 5a-h, 9a-e and azides 4, 8a,b respectively. On the other hand, azide 4 underwent Curtius rearrangement to the corresponding isocyanate which subsequently reacted with selected aliphatic and/or aniline derivatives to give the corresponding urea derivatives 11 and 12a, b. Also reaction of isocyanate with secondary amines gave amide derivatives 13a, b.
Keywords: triazoles, amino acids, azide coupling, peptides, Curtius

 

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