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首页> 外文期刊>RSC Advances >Nitrones and nucleobase-containing spiro-isoxazolidines derived from isatin and indanone: solvent-free microwave-assisted stereoselective synthesis and theoretical calculations
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Nitrones and nucleobase-containing spiro-isoxazolidines derived from isatin and indanone: solvent-free microwave-assisted stereoselective synthesis and theoretical calculations

机译：源自靛红和茚满酮的亚硝基和含核碱基的螺-异恶唑烷：无溶剂微波辅助立体选择性合成和理论计算

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摘要

The spiro-oxindoles have found wide application because of their antiviral properties. However, in the literature few examples of synthesis of their precursors, oxindole-nitrones, are reported. In this paper, we initially present a rapid and efficient synthetic approach to ketonitrones by solvent-free microwave-assisted reaction between isatin or indanone derivatives and various hydroxylamines. The synthetic protocol is facile, clean, fast, high-yielding and stereoselective. Then, we explored the possibility to synthesize nucleobase-containing spiro-isoxazolidines with isatin and indanone nuclei by solvent-free MW-assisted 1,3-dipolar cycloaddition, obtaining good results in yields (74–85%), and regio- and diastereoselectivity. Theoretical calculations were done to analyze the difference of reactivity of isatin and indanone derivatives with hydroxylamines.
机译：螺-羟吲哚由于其抗病毒特性而被广泛应用。然而，在文献中很少报道其前体羟吲哚-硝酮的合成的实例。在本文中，我们最初提出了一种快速，高效的合成方法，该方法通过Isatin或茚满酮衍生物与各种羟胺之间的无溶剂微波辅助反应来合成酮硝酮。合成规程是容易，干净，快速，高产量和立体选择性的。然后，我们探索了通过无溶剂的MW辅助1,3-偶极环加成合成含核苷的螺-异​​恶唑烷与靛红和茚满酮核的可能性，获得了良好的收率（74–85％），以及区域和非对映选择性。进行了理论计算以分析伊斯丁和茚满酮衍生物与羟胺的反应性差异。

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