Synthesis of 3, 5-disubstituted-1, 2, 4-oxadiazoles using tetrabutylammonium fluoride as a mild and efficient catalyst

AR Gangloff, J Litvak, EJ Shelton, D Sperandio…

Index: Gangloff, Anthony R.; Litvak, Joane; Shelton, Emma J.; Sperandio, David; Wang, Vivian R.; Rice, Kenneth D. Tetrahedron Letters, 2001 , vol. 42, # 8 p. 1441 - 1443

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Citation Number: 122

Abstract

Tetrabutylammonium fluoride (TBAF) was found to be a mild and efficient catalyst for the synthesis of 3, 5-disubstituted-1, 2, 4-oxadiazoles. Using 0.1–1.0 equivalents of TBAF in THF for 1–24 h at room temperature, alkanoyl-and aroyloxyamidines were converted in high yield to the corresponding 3, 5-disubstituted-1, 2, 4-oxadiazoles. A variety of R and R′ substituents were investigated.