A mild, one-pot synthesis of 3-cyano-4-benzopyrones from 2-hydroxyacetophenones

Reddy, Gopal; Latha, D.; Thirupathaiah, C.; Rao, K. Srinivasa

doi:10.1016/j.tetlet.2003.11.023

Cited by 27 publications

(5 citation statements)

References 13 publications

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“…The formylation reagent, known as Vilsmeier or Vilsmeier–Haack reagent, is formed in situ from DMF and a chlorinating agent, with POCl 3 being the most common. The Vilsmeier reagent has been widely used for formylation, chlorination, chloroformylation, and cyclization, among other reactions . Despite the convenience of the Vilsmeier reagent, the scale-up of the reaction is troublesome due to its instability.…”

Section: Introductionmentioning

confidence: 99%

A Vilsmeier Chloroformylation by Continuous Flow Chemistry

Carrera

Coen

Coppens

et al. 2020

Org. Process Res. Dev.

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Chloroformylation reactions are versatile reactions that allow the introduction of a chlorine atom and an aldehyde group in enolizable ketones, employing the well-known Vilsmeier reagent. However, the use of this unstable reagent is usually associated with hazards, especially when it is used on an industrial scale. The present article describes the preparation and use of the Vilsmeier reagent under continuous flow conditions for the preparation of an important intermediate in the synthesis of cyanine dyes. In addition, the traditionally used dimethylformamide has been substituted with more desirable formamides, together with the removal of the halogenated solvent usually employed in the reaction. Consequently, the optimized conditions allow the continuous production of the target compound in a 79–81% isolated yield in a more environmentally friendly, fast, and secure manner.

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Section: Introductionmentioning

confidence: 99%

A Vilsmeier Chloroformylation by Continuous Flow Chemistry

Carrera

Coen

Coppens

et al. 2020

Org. Process Res. Dev.

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“…N -Cyclopropylanilines 2 were synthesized according to the literature procedure . 3-Cyanochromones 1 were prepared from the corresponding starting materials following the literature procedure …”

Section: Methodsmentioning

confidence: 99%

“… 14 3-Cyanochromones 1 were prepared from the corresponding starting materials following the literature procedure. 15 …”

Section: Methodsmentioning

confidence: 99%

Visible Light Promoted [3+2]-Cycloaddition for the Synthesis of Cyclopenta[b]chromenocarbonitrile Derivatives

Kowalska,

Dyguda,

Artelska

et al. 2023

J. Org. Chem.

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In the manuscript, a novel method for the preparation of cyclopenta[ b ]chromenocarbonitrile derivatives via [3+2] cycloaddition reaction of substituted 3-cyanochromones and N -cyclopropyloamines initiated by visible light catalysis has been described. The reaction was performed in the presence of Eosin Y as a photocatalyst. The key parameters responsible for the success of the described strategy are visible light, a small amount of photoredox catalyst, an anhydrous solvent, and an inert atmosphere.

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“…[7] However, few studies have documented the preparation of 3-substituted chromones. Moreover, relatively few reports have focused on electron-withdrawing groups at the 3rd position of substituted chromones, such as 3-formyl, [8] 3-acyl, [9] 3nitro, [10] 3-CF 3 , [11] 3-cyano, [12] and 3-sulfonyl. [13] According to our previous report, among these electrondeficient groups, only 3-sulfonyl-substituted chromone has exhibited a series of interesting activities for inhibiting the growth of oral cancer cells.…”

Section: Introductionmentioning

confidence: 99%

(CF₃CO)₂O/K₂CO₃‐Mediated Synthesis of 3‐Sulfonylchromones through Cyclocondensation of β‐Ketosulfones and Carboxylic Acids

Chang

Lin

2023

Adv Synth Catal

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One‐pot (CF3CO)2O/K2CO3‐mediated tandem cyclocondensation of β‐ketosulfones with carboxylic acids provides diversified 3‐sulfonylchromones in good to excellent yields by refluxing MeCN under high‐pressure (using a sealed tube) and dry‐nitrogen atmospheric conditions. This study proposed and discussed a plausible mechanism. The paper also described the formation of 3‐sulfonylflavones and gram‐scale synthesis of 3‐sulfonylchromones. Various combinations of anhydrides and bases‐promoted reaction conditions were investigated for the (4+2) annulation via one carbon‐oxygen (C−O) bond and one carbon‐carbon (C=C) bond formations.

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A mild, one-pot synthesis of 3-cyano-4-benzopyrones from 2-hydroxyacetophenones

Cited by 27 publications

References 13 publications

A Vilsmeier Chloroformylation by Continuous Flow Chemistry

A Vilsmeier Chloroformylation by Continuous Flow Chemistry

Visible Light Promoted [3+2]-Cycloaddition for the Synthesis of Cyclopenta[b]chromenocarbonitrile Derivatives

(CF₃CO)₂O/K₂CO₃‐Mediated Synthesis of 3‐Sulfonylchromones through Cyclocondensation of β‐Ketosulfones and Carboxylic Acids

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A mild, one-pot synthesis of 3-cyano-4-benzopyrones from 2-hydroxyacetophenones

Cited by 27 publications

References 13 publications

A Vilsmeier Chloroformylation by Continuous Flow Chemistry

A Vilsmeier Chloroformylation by Continuous Flow Chemistry

Visible Light Promoted [3+2]-Cycloaddition for the Synthesis of Cyclopenta[b]chromenocarbonitrile Derivatives

(CF3CO)2O/K2CO3‐Mediated Synthesis of 3‐Sulfonylchromones through Cyclocondensation of β‐Ketosulfones and Carboxylic Acids

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(CF₃CO)₂O/K₂CO₃‐Mediated Synthesis of 3‐Sulfonylchromones through Cyclocondensation of β‐Ketosulfones and Carboxylic Acids