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

被引：10

作者：

Huang, Lang ^{[1
]}

Yao, Zhenyu ^{[1
]}

Huang, Guanghua ^{[1
]}

Ao, Yaqi ^{[1
]}

Zhu, Bin ^{[1
]}

Li, Sanshu ^{[1
]}

Cui, Xiuling ^{[1
]}

机构：

[1] Huaqiao Univ, Sch Biomed Sci, Key Lab Xiamen Marine & Gene Drugs,Engn Res Ctr M, Minist Educ,Key Lab Fujian Mol Med,Key Lab Precis, Xiamen 361021, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2021年 / 363卷 / 22期

关键词：

azaoxyallyl cations; gold catalysis; cycloaddition reaction; nucleic acid dye; fused indolin-3-ones; FORMED AZAOXYALLYL CATIONS; AZA-OXYALLYL CATIONS; NITROALKYNE REDOX; ACCESS; ANNULATION; DERIVATIVES; CONSTRUCTION; CYCLIZATION; SKELETON; CASCADE;

D O I：

10.1002/adsc.202100842

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A formal [3+3] cycloaddition reaction of azaoxyallyl cations and isatogens generated in situ from alpha-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.

引用

页码：5092 / 5098

页数：7

共 66 条

[21] Recent Advances in Gold-Catalyzed N- and O-Functionalizations of Alkynes with Nitrones, Nitroso, Nitro and Nitroxy Species [J].