Electro- and Mechanochemical Strategy as a Dual Synthetic Approach for Biologically Relevant 3-Nitro-imidazo-[1,2-<i>a</i>]pyridines

We herein disclose a dual synthetic approach involving electrochemical and mechanochemical strategies for diversely functionalized 3-nitro-2-aryl-immidazo[1,2-<i>a</i>]pyridines. Both methods offer a practical and straightforward alternative route for accessing this important class of biologically promising nitrogen-containing heterocycles. Significant advantages of the newly developed methods include mild and energy-efficient reaction conditions, avoidance of transition metal catalysts, external heating and additional oxidants, shorter reaction times, good to excellent yields, broad substrate scope, gram-scale applicability, operational simplicity, and eco-friendliness. Furthermore, a synthetic application was extended by successfully reducing synthesized 3-nitro-2-aryl-immidazo[1,2-<i>a</i>]pyridines to their corresponding amino derivatives.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-08-15
DOI
https://doi.org/10.1021/acs.joc.4c00881
Citations
15
Primary Topic
Phenothiazines and Benzothiazines Synthesis and Activities
Type
article
Field-Weighted Citation Impact
3.51

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article

Electro- and Mechanochemical Strategy as a Dual Synthetic Approach for Biologically Relevant 3-Nitro-imidazo-[1,2-a]pyridines

Goutam Brahmachari, Indrajit Karmakar, Debojyoti Mukherjee
15 citations
The Journal of Organic Chemistry
Phenothiazines and Benzothiazines Synthesis and Activities
3.51
article

Electro- and Mechanochemical Strategy as a Dual Synthetic Approach for Biologically Relevant 3-Nitro-imidazo-[1,2-a]pyridines

Goutam Brahmachari, Indrajit Karmakar, Debojyoti Mukherjee
article en
15 citations

Abstract

We herein disclose a dual synthetic approach involving electrochemical and mechanochemical strategies for diversely functionalized 3-nitro-2-aryl-immidazo[1,2-<i>a</i>]pyridines. Both methods offer a practical and straightforward alternative route for accessing this important class of biologically promising nitrogen-containing heterocycles. Significant advantages of the newly developed methods include mild and energy-efficient reaction conditions, avoidance of transition metal catalysts, external heating and additional oxidants, shorter reaction times, good to excellent yields, broad substrate scope, gram-scale applicability, operational simplicity, and eco-friendliness. Furthermore, a synthetic application was extended by successfully reducing synthesized 3-nitro-2-aryl-immidazo[1,2-<i>a</i>]pyridines to their corresponding amino derivatives.

The Journal of Organic ChemistryVol. 89(17)
Visva-Bharati University (IN)
Science and Engineering Research Board
Openalex Percentile: Top 7%
Phenothiazines and Benzothiazines Synthesis and Activities
3.51
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