Acid-Mediated Synthesis of Chromeno[2,3-b]pyridine Derivatives via Condensation of 2-Amino-3-formylchromones and 1-(Methylthio)-2-nitroenamine Derivatives

Yang, Hongchen; Zhang, Lu; Xu, Xiaoyong; Qiao, Zhi; Li, Zhong

doi:10.1055/a-1790-2992

Synlett

2022

DOI: 10.1055/a-1790-2992

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Acid-Mediated Synthesis of Chromeno[2,3-b]pyridine Derivatives via Condensation of 2-Amino-3-formylchromones and 1-(Methylthio)-2-nitroenamine Derivatives

Hongchen Yang

Lu Zhang

Xiaoyong Xu

et al.

Abstract: A convenient and effective protocol has been proposed for the synthesis of chromeno[2,3-b]pyridine derivatives via the CF3SO3H-catalyzed annulation of substituted 2-amino-3-formylchromones and various 1-(methylthio)-2-nitroenamine derivatives. This method is time-efficient, convenient, high-yielding, and exhibits a good functional group compatibility.

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DBU-Mediated Domino Annulation Reaction of 2-Amino-4H-chromen-4-ones and Aromatic Aldehydes for Synthesis of Polysubstituted 3-Hydroxy-5H-chromeno[2,3-b]pyridinones

Xin

Xue

et al. 2022

J. Org. Chem.

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A pseudo-three-component annulation reaction of substituted 2-amino-4H-chromen-4-ones with aromatic aldehydes promoted by DBU was investigated to access polysubstituted 5H-chromeno[2,3-b]pyridines. This reaction included a sequential intermolecular nucleophilic addition/Michael cyclization/intramolecular epoxidation/ring opening/aromatization sequence, which possessed excellent step and atom economy in a single operation for generating 3-hydroxy-5H-chromeno[2,3-b]pyridines from readily available substrates.

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DBU-Mediated Domino Annulation Reaction of 2-Amino-4H-chromen-4-ones and Aromatic Aldehydes for Synthesis of Polysubstituted 3-Hydroxy-5H-chromeno[2,3-b]pyridinones

Xin

Xue

et al. 2022

J. Org. Chem.

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Synthetic Methods for Various Chromeno-fused Heterocycles and their Potential as Antimicrobial Agents

Agrawal,

Goswami,

Pathak

2024

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Chromenes are a significant family of heterocyclic chemicals that have a wide range of biological applications, a simple chemical structure, and only mildly undesirable side effects. The synthesis of a wide range of chromene analogs that displayed unexpected behaviors via numerous mechanisms was investigated by a number of different research teams, which led to the discovery of multiple pathways for their synthesis. In addition, different chromene-fused heterocycles exhibit a wide variety of fascinating biological actions, including those that are anticancer, anticonvulsant, antibacterial, anticholinesterase, antituberculosis, and anti-diabetic. In light of this, the purpose of this study is to highlight the many synthesis techniques and antibacterial activity associated with chromene-fused heterocyclic compounds. Moreover, such research can open avenues for exploring other therapeutic applications of these compounds in various disease areas, as their biological activities extend beyond antibacterial effects.

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Acid-Mediated Synthesis of Chromeno[2,3-b]pyridine Derivatives via Condensation of 2-Amino-3-formylchromones and 1-(Methylthio)-2-nitroenamine Derivatives

Cited by 2 publications

References 29 publications

DBU-Mediated Domino Annulation Reaction of 2-Amino-4H-chromen-4-ones and Aromatic Aldehydes for Synthesis of Polysubstituted 3-Hydroxy-5H-chromeno[2,3-b]pyridinones

DBU-Mediated Domino Annulation Reaction of 2-Amino-4H-chromen-4-ones and Aromatic Aldehydes for Synthesis of Polysubstituted 3-Hydroxy-5H-chromeno[2,3-b]pyridinones

Synthetic Methods for Various Chromeno-fused Heterocycles and their Potential as Antimicrobial Agents

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