A simple and efficient procedure for synthesis of optically active 1,3,4-oxadiazole derivatives containing L-amino acid moieties

Some new unsymmetrical and optically active 2,5-disubstituted 1,3,4-oxadiazoles 5a-j were efficiently synthesized by cyclization reaction of diacylhydrazides 4a-j. The synthesis of the title compounds was achieved by the reaction of acyl hydrazides 3a-b and N-phetaloyl-L-amino acids 1a-e in the presence of the phosphoroxy chloride (POCl3) as an anhydrous reagent.

Anahtar Kelimeler:

N-phetaloyl-L-amino acid, 1, 3, 4-oxadiazole, diacylhydrazide, pyridoyl hydrazide, phosphoroxy chloride

A simple and efficient procedure for synthesis of optically active 1,3,4-oxadiazole derivatives containing L-amino acid moieties

Keywords:

N-phetaloyl-L-amino acid, 1, 3, 4-oxadiazole, diacylhydrazide, pyridoyl hydrazide, phosphoroxy chloride,

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We synthesized some N-phetaloyl-L-amino acylchlorides having a free terminal carboxyl function, which can react with pyridoyl hydrazides at room temperature to give the intermediates 4a-j. Then these intermediates are cyclized to 5a-j at room temperature. This reaction may be useful for combinational synthesis of type 5 compounds having various R and Ar substituents with a view to test for biological activities. Shawali, A. S.; Abdallah, M. A.; Zayed, M. E. M. Eur. J. Med. Chem. 2009, 44, 2106-2112.
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