Solid-Phase Organic Synthesis of Vinyl-Substituted 1,3,4-Oxadiazoles Using Polymer-Bound α-Selenopropionic Acid

Abstract

Vinyl-substituted 1,3,4-oxadiazoles can be efficiently synthesized through acylation, cyclocondensation, and oxidation–elimination reaction from polystyrene-supported α-selenopropionic acid and acid hydrazides. This new solid-phase organic synthesis method could provide the target compounds in good yield and purity, with advantages of decreased volatility and simplification of workup procedure.

Keywords:

• Polystyrene-supported α-selenopropionic acid
• solid-phase organic synthesis
• vinyl-substituted 1
• 3
• 4-oxadiazole

ACKNOWLEDGMENT

We gratefully acknowledge financial support from the National Natural Science Foundation of China (No. 20562005) and NSF of Jiangxi Province (Nos. 0620021 and 2007GZW0185).

Notes

^a Overall yields based on polystyrene-supported α-selenopropionic acid 2 (1.20 mmol COOH/g).

^b Determined by HPLC (high-performance liquid chromatography) of crude cleavage product (λ = 254 nm).