One-Pot Synthesis of Fused Indolin-3-Ones via a [3+3] Cycloaddition Reaction,Advanced Synthesis & Catalysis

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One-Pot Synthesis of Fused Indolin-3-Ones via a [3+3] Cycloaddition Reaction
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2021-09-07 , DOI: 10.1002/adsc.202100842
Lang Huang ₁ , Zhenyu Yao ₁ , Yaqi Ao ₁ , Bin Zhu ₁ , Sanshu Li ₁ , Xiuling Cui ₂

Affiliation

A formal [3+3] cycloaddition reaction of azaoxyallyl cations and isatogens generated in situ from α-halo hydroxamates and o-nitroalkynes, respectively, was developed. The cycloisomerization of the o-nitroalkynes, followed by base-mediated elimination of hydrogen halide and 1,3-dipolar cycloaddition of the azaoxyallyl cations with the isatogen intermediates, were hallmarks of this one-pot tandem reaction. A series of tricyclic fused indolin-3-ones were obtained under very mild reaction conditions with high atom economy, and the reaction exhibited excellent functional group tolerance. In addition, the reaction was highly scalable to multigram quantities. The obtained indolin-3-ones exhibited robust DNA staining patterns in agarose gel electrophoresis. Coupled with the fluorescence properties of the products, these results highlight the potential utility of tricyclic fused indolin-3-ones in various fluorescence and cell-staining applications.

中文翻译：

通过 [3+3] 环加成反应一锅法合成融合的 Indolin-3-Ones

分别由α-卤代异羟肟酸酯和邻硝基炔烃原位生成的氮杂氧基烯丙基阳离子和靛蓝原位的正式[3+3]环加成反应被开发出来。o的环异构化-硝基炔烃，然后是碱介导的卤化氢消除和氮杂氧基烯丙基阳离子与靛蓝中间体的 1,3-偶极环加成反应，是这种一锅串联反应的标志。在非常温和的反应条件下，获得了一系列具有高原子经济性的三环稠合吲哚啉-3-酮，该反应表现出优异的官能团耐受性。此外，该反应可高度扩展至数克数量。获得的 indolin-3-ones 在琼脂糖凝胶电泳中表现出强大的 DNA 染色模式。结合产品的荧光特性，这些结果突出了三环稠合 indolin-3-ones 在各种荧光和细胞染色应用中的潜在效用。

更新日期：2021-09-07

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