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Synthesis of sulfonyloxy furoxans via hydroxyfuroxan ammonium salts
Tetrahedron ( IF 2.1 ) Pub Date : 2018-05-11 , DOI: 10.1016/j.tet.2018.05.029
Ryosuke Matsubara , Yuki Katsuragi , Takaya Sakaguchi , Shuhei Eguchi , Masahiko Hayashi , Akihiro Ando

Furoxans are distinctive heteroaromatic compounds in that they are potentially capable of releasing nitric oxide under physiological conditions. In order to utilize the furoxan scaffold for the development of functional molecules, synthetically relevant functional groups are required for access to diverse furoxans. In this report, a facile route to furoxans with sulfonyloxy groups, which are halide surrogates, has been developed. The key features of this strategy include the synthesis and utilization of bench-stable hydroxyfuroxan salts, the use of sulfonyl anhydrides in the sulfonylation step instead of sulfonyl chlorides, and the photochemical isomerization of one regioisomer to another in order to gain access to both.



中文翻译:

羟基呋喃烷铵盐合成磺酰氧基呋喃烷

呋喃喃类化合物是独特的杂芳族化合物,因为它们在生理条件下具有释放一氧化氮的潜在能力。为了利用呋喃聚糖支架开发功能性分子,需要合成相关的官能团来获得各种呋喃酮。在该报告中,已经开发了一种容易的路线,可生产具有磺酰氧基的呋喃喃,该磺酰氧基是卤素替代物。该策略的关键特征包括合成和利用稳定的羟基呋喃喃盐,在磺酰化步骤中使用磺酰酐代替磺酰氯,以及将一种区域异构体进行光化学异构化以使其同时进入另一区域。

更新日期:2018-05-11
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