AlCl3-Mediated Synthesis of 4-Aryl-2-quinolone-3-carboxylates

Yang, Seung-Hye; Jo, Seohyun; Shin, Dongyun

doi:10.1055/s-0036-1588798

Cited by 6 publications

(1 citation statement)

References 23 publications

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“…The 1a – 1r was synthesized according to the previous literature . In general, to a solution of aniline (10 mmol) and triethylamine (20 mmol) in dichloromethane (20 mL) at 0 °C was added dropwise a solution of acid chloride (10 mmol) in dichloromethane (20 mL).…”

Section: Methodsmentioning

confidence: 99%

Triphosgene and Triphenylphosphine Oxide-Mediated Cascade Heterocyclization of N-Acylated Anilines: One-Pot Synthesis of 2,4-Dichloroquinolines

Feng,

Xu,

Wang

et al. 2023

J. Org. Chem.

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A one-pot cascade chlorination/heterocyclization strategy has been developed for the synthesis of 2,4-dichlorosubstituted quinolines from acylated anilines using triphosgene and triphenylphosphine oxide. Obviating the conventional harsh conditions of chlorination, synthetic useful quinolines with moderate to good yields were obtained through this reaction. The mechanism study exhibited that the formation of a β-enamine intermediate plays a vital role in the generation of the final product.

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Section: Methodsmentioning

confidence: 99%

Triphosgene and Triphenylphosphine Oxide-Mediated Cascade Heterocyclization of N-Acylated Anilines: One-Pot Synthesis of 2,4-Dichloroquinolines

Feng,

Xu,

Wang

et al. 2023

J. Org. Chem.

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Convenient Synthesis of Pyrano[3,2‐g]chromene‐6‐ones from Naturally Occurring Visnagin and Evaluation of their Antimicrobial Activity

Alhadhrami,

Al‐Harbi,

Abbas

2024

ChemistrySelect

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It is well known that chromones possess numerous of biological activities. Due to their significant applications, there are increasing for synthesizing of several chromones but few pyranochromene have been synthesized. So, simple and convenient routes for the synthesizing of new pyrano[3,2‐g]chromenone derivatives in high yields were illustrated using visnagin as starting naturally occurring. Ring opening of visnagin afforded 6‐formyl‐7‐hydroxychromone derivative which was subjected to react with variety of active methlyene derivatives to afford pyrano[3,2‐g]chromenone derivatives. Thus, heating of 6‐formylchromone with aroylacetate gave the 3‐(aroyl)‐pyranochromene‐2,6‐dione. The desired pyranochromene‐3‐carboxamide derivatives were obtained when the precursor 6‐formylchromone was condensed with ethyl 3‐oxo‐3‐(arylamino)propanoates. When 6‐formylchromone was condensed with hippuric acid gave oxazolone derivative rather than pyranochromene derivative. Condensation of 6‐formylchromone with cyanothioacetamide led to the formation of thioamide derivative. 2‐Iminopyranochromene derivatives were synthesized through reaction of 6‐formylchromone with diverse cyanoacetamide derivatives. Finally, reaction of 6‐formylchromone with 3‐(dimethylpyrazolyl)‐3‐oxopropanenitrile gave 3‐cyano‐pyranochromenedione rather than pyrazole derivative. Antimicrobial activity of the synthesized pyranochromenone derivatives was evaluated. Nearly all compounds showed weak effects towards B. subtilis and P. vulgaris. All compounds showed no effects towards S. aureus and E. coli. All compounds showed no effects towards all tested fungi except thioamide derivative 6 showed moderate activity.

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One-pot synthesis of 2-acylbenzothiazoles from 2-aminobenzenethiols and arylacetonitriles via cyclization and sequential oxidation

Zhang

Wang

Leng

et al. 2021

Tetrahedron Letters

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AlCl3-Mediated Synthesis of 4-Aryl-2-quinolone-3-carboxylates

Cited by 6 publications

References 23 publications

Triphosgene and Triphenylphosphine Oxide-Mediated Cascade Heterocyclization of N-Acylated Anilines: One-Pot Synthesis of 2,4-Dichloroquinolines

Triphosgene and Triphenylphosphine Oxide-Mediated Cascade Heterocyclization of N-Acylated Anilines: One-Pot Synthesis of 2,4-Dichloroquinolines

Convenient Synthesis of Pyrano[3,2‐g]chromene‐6‐ones from Naturally Occurring Visnagin and Evaluation of their Antimicrobial Activity

One-pot synthesis of 2-acylbenzothiazoles from 2-aminobenzenethiols and arylacetonitriles via cyclization and sequential oxidation

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