1,3,4-Oxadiazole formation; a novel solid support strategy
β Scribed by John P Kilburn; Jesper Lau; Raymond C.F Jones
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 92 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
A new approach to the synthesis of 1,3,4-oxadiazoles on solid support is described. Resin bound 1-acyl thiosemicarbazides were treated with a variety of dehydrating agents at different temperatures, which revealed that thiosemicarbazides were effectively cyclised by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCβ’HCl); mild acidic cleavage from the solid support released the substituted 1,3,4-oxadiazoles in excellent purity.
π SIMILAR VOLUMES
Automated solid phase synthesis of 2'-deoxyribose oligonucleotides; d(Tp)7T, d(Tps)TT and d(Tp)3(CBZp)2(Tp)2T, was achieved directly in 99% overall yields using a novel silyl linkage to a CPG silica support cleavable within seconds at room temperature using TBAF.