Efficient one-pot synthesis of substituted 2-amino-1,3,4-oxadiazoles

A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles is described. A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles has been developed. The method is a significant improvement over previously reported syntheses. Reaction of...

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Bibliographic Details
Published inTetrahedron letters Vol. 49; no. 47; pp. 6709 - 6711
Main Authors Piatnitski Chekler, Eugene L., Elokdah, Hassan M., Butera, John
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.11.2008
Elsevier
Subjects
Chemistry
Chemistry, Organic
Kinase inhibitor
One-pot cyclization
Oxadiazole
Physical Sciences
Science & Technology
Oxadiazole
Kinase inhibitor
One-pot cyclization
ACID
DERIVATIVES
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Summary:A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles is described. A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles has been developed. The method is a significant improvement over previously reported syntheses. Reaction of carboxylic acids with thiosemicarbazides afforded the corresponding oxadiazoles in moderate to good yields. In general, the products precipitated from the reaction mixture, and were collected by filtration. In most of the cases, no chromatographic separations were required. To explore the scope and limitations of this reaction, various aliphatic, aromatic, and heteroaromatic carboxylic acids were reacted with different substituted thiosemicarbazides. The influence of R 1 and R 2 substituents on the reaction yield and additional results demonstrating the versatility of this method are presented.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.09.057