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Novel Eco-friendly, One-Pot Method for the Synthesis of Kynurenic Acid Ethyl Esters

[Image: see text] The synthesis of kynurenic acid derivatives with potential biological effect was investigated and optimized for one-batch, two-step microwave-assisted reactions. Utilizing both chemically and biologically representative non-, methyl-, methoxy-, and chlorosubstituted aniline derivat...

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Autores principales: Simon, Péter, Lőrinczi, Bálint, Hetényi, Anasztázia, Szatmári, István
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10210203/
https://www.ncbi.nlm.nih.gov/pubmed/37251176
http://dx.doi.org/10.1021/acsomega.3c01170
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author Simon, Péter
Lőrinczi, Bálint
Hetényi, Anasztázia
Szatmári, István
author_facet Simon, Péter
Lőrinczi, Bálint
Hetényi, Anasztázia
Szatmári, István
author_sort Simon, Péter
collection PubMed
description [Image: see text] The synthesis of kynurenic acid derivatives with potential biological effect was investigated and optimized for one-batch, two-step microwave-assisted reactions. Utilizing both chemically and biologically representative non-, methyl-, methoxy-, and chlorosubstituted aniline derivatives, in catalyst-free conditions, syntheses of seven kynurenic acid derivatives were achieved in a time frame of 2–3.5 h. In place of halogenated reaction media, tuneable green solvents were introduced for each analogue. The potential of green solvent mixtures to replace traditional solvents and to alter the regioisomeric ratio regarding the Conrad–Limpach method was highlighted. The advantages of the fast, eco-friendly, inexpensive analytic technique of TLC densitometry were emphasized for reaction monitoring and conversion determination in comparison to quantitative NMR. Moreover, the developed 2–3.5 h syntheses were scaled-up to achieve gram-scale products of KYNA derivatives, without altering the reaction time in the halogenated solvent DCB and more importantly in its green substitutes.
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spelling pubmed-102102032023-05-26 Novel Eco-friendly, One-Pot Method for the Synthesis of Kynurenic Acid Ethyl Esters Simon, Péter Lőrinczi, Bálint Hetényi, Anasztázia Szatmári, István ACS Omega [Image: see text] The synthesis of kynurenic acid derivatives with potential biological effect was investigated and optimized for one-batch, two-step microwave-assisted reactions. Utilizing both chemically and biologically representative non-, methyl-, methoxy-, and chlorosubstituted aniline derivatives, in catalyst-free conditions, syntheses of seven kynurenic acid derivatives were achieved in a time frame of 2–3.5 h. In place of halogenated reaction media, tuneable green solvents were introduced for each analogue. The potential of green solvent mixtures to replace traditional solvents and to alter the regioisomeric ratio regarding the Conrad–Limpach method was highlighted. The advantages of the fast, eco-friendly, inexpensive analytic technique of TLC densitometry were emphasized for reaction monitoring and conversion determination in comparison to quantitative NMR. Moreover, the developed 2–3.5 h syntheses were scaled-up to achieve gram-scale products of KYNA derivatives, without altering the reaction time in the halogenated solvent DCB and more importantly in its green substitutes. American Chemical Society 2023-05-11 /pmc/articles/PMC10210203/ /pubmed/37251176 http://dx.doi.org/10.1021/acsomega.3c01170 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Simon, Péter
Lőrinczi, Bálint
Hetényi, Anasztázia
Szatmári, István
Novel Eco-friendly, One-Pot Method for the Synthesis of Kynurenic Acid Ethyl Esters
title Novel Eco-friendly, One-Pot Method for the Synthesis of Kynurenic Acid Ethyl Esters
title_full Novel Eco-friendly, One-Pot Method for the Synthesis of Kynurenic Acid Ethyl Esters
title_fullStr Novel Eco-friendly, One-Pot Method for the Synthesis of Kynurenic Acid Ethyl Esters
title_full_unstemmed Novel Eco-friendly, One-Pot Method for the Synthesis of Kynurenic Acid Ethyl Esters
title_short Novel Eco-friendly, One-Pot Method for the Synthesis of Kynurenic Acid Ethyl Esters
title_sort novel eco-friendly, one-pot method for the synthesis of kynurenic acid ethyl esters
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10210203/
https://www.ncbi.nlm.nih.gov/pubmed/37251176
http://dx.doi.org/10.1021/acsomega.3c01170
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