A substrate-induced dual utilization cascade reaction of <i>N</i>-alkyl anilines: highly site-selective sustainable synthesis of chromeno[4,3-<i>b</i>]quinolin-6-ones

We describe a novel substrate-induced cascade reaction of <i>N</i>-alkyl anilines <i>via</i> C(sp<sup>3</sup>)-N bond cleavage and reorganization into chromeno[4,3-<i>b</i>]quinolin-6-ones. <i>N</i>-alkyl anilines are not only used as a carbon source, but also the waste group was trapped by 4-hydroxy coumarin. The calculation of green metrics shows that our protocol is more efficient and green with lower emission than before. Additionally, a gram-scale reaction and one-pot synthesis of bioactive molecules further demonstrate the potential application of our protocol in the pharmaceutical industry.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2024-11-29
DOI
https://doi.org/10.1039/d4ob01764a
Citations
1
Primary Topic
Multicomponent Synthesis of Heterocycles
Type
article
Field-Weighted Citation Impact
0.25

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article

A substrate-induced dual utilization cascade reaction of N-alkyl anilines: highly site-selective sustainable synthesis of chromeno[4,3-b]quinolin-6-ones

Guiyun Zeng, Chao Huang, Minglong Yuan, Zhou Zhang et al.
1 citations
Organic & Biomolecular Chemistry
Multicomponent Synthesis of Heterocycles
0.25
article

A substrate-induced dual utilization cascade reaction of N-alkyl anilines: highly site-selective sustainable synthesis of chromeno[4,3-b]quinolin-6-ones

Guiyun Zeng, Chao Huang, Minglong Yuan, Zhou Zhang, Yuanmin Wen, Sihan Zhao
article en
1 citations

Abstract

We describe a novel substrate-induced cascade reaction of <i>N</i>-alkyl anilines <i>via</i> C(sp<sup>3</sup>)-N bond cleavage and reorganization into chromeno[4,3-<i>b</i>]quinolin-6-ones. <i>N</i>-alkyl anilines are not only used as a carbon source, but also the waste group was trapped by 4-hydroxy coumarin. The calculation of green metrics shows that our protocol is more efficient and green with lower emission than before. Additionally, a gram-scale reaction and one-pot synthesis of bioactive molecules further demonstrate the potential application of our protocol in the pharmaceutical industry.

Organic & Biomolecular ChemistryVol. 23(4)
Minzu University of China (CN)
National Natural Science Foundation of China, Yunnan Provincial Department of Education
Openalex Percentile: Top 46%
Multicomponent Synthesis of Heterocycles
0.25
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