Solution versus Fluorous versus Solid-Phase Synthesis of 2,5-Disubstituted 1,3-Azoles. Preliminary Antibacterial Activity Studies
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- 作者：Juan F. Sanz-Cervera ; Ral Blasco ; Julio Piera ; Michael Cynamon ; Ignacio Ibez ; Marcelo Murgua ; Santos Fustero
- 刊名：Journal of Organic Chemistry
- 出版年：2009
- 出版时间：December 4, 2009
- 年：2009
- 卷：74
- 期：23
- 页码：8988-8996
- 全文大小：942K
- 年卷期：v.74,no.23(December 4, 2009)
- ISSN：1520-6904
文摘
A small library of compounds with an oxa(thia)zole scaffold and structural diversity in both positions 2 and 5 has been synthesized. Double acylation of a protected glycine affords intermediate α-amido-β-ketoesters, which in turn can be dehydrated to afford 1,3-oxazoles or reacted with Lawesson’s reagent to furnish 1,3-thiazoles. This procedure was designed with its adaptation to fluorous techniques in mind. Thus, when a protected glycine with a fluorous tag in the ester moiety is used as a starting material, the synthesis can be easily completed without column chromatography purification of intermediate compounds with good to excellent yields, thus affording a suitable entry to the preparation of small libraries of these bioactive compounds. The prepared oxa(thia)zoles were assayed for their antibacterial activity, and several of them were active against Staphylococcus aureus.