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A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives

Quinolone is a privileged scaffold in medicinal chemistry and 4-Quinolone-3-Carboxamides have been reported to harbor vast therapeutic potential. However, conversion of N-1 substituted 4-Quinolone 3-Carboxylate to its corresponding carbamates is highly restrictive. This motivated us to adopt a much...

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Autores principales: Gill, Muhammad Shoaib Ali, Azzman, Nursyuhada, Hassan, Sharifah Syed, Shah, Syed Adnan Ali, Ahemad, Nafees
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer International Publishing 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9733071/
https://www.ncbi.nlm.nih.gov/pubmed/36482476
http://dx.doi.org/10.1186/s13065-022-00902-1
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author Gill, Muhammad Shoaib Ali
Azzman, Nursyuhada
Hassan, Sharifah Syed
Shah, Syed Adnan Ali
Ahemad, Nafees
author_facet Gill, Muhammad Shoaib Ali
Azzman, Nursyuhada
Hassan, Sharifah Syed
Shah, Syed Adnan Ali
Ahemad, Nafees
author_sort Gill, Muhammad Shoaib Ali
collection PubMed
description Quinolone is a privileged scaffold in medicinal chemistry and 4-Quinolone-3-Carboxamides have been reported to harbor vast therapeutic potential. However, conversion of N-1 substituted 4-Quinolone 3-Carboxylate to its corresponding carbamates is highly restrictive. This motivated us to adopt a much simpler, scalable and efficient methodology for the synthesis of highly pure N-1 substituted 4- Quinolone-3-Carboxamides with excellent yields. Our adopted methodology not only provides a robust pathway for the convenient synthesis of N-1 substituted 4- Quinolone-3-Carboxamides which can then be explored for their therapeutic potential, this may also be adaptable for the derivatization of other such less reactive carboxylate species. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s13065-022-00902-1.
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spelling pubmed-97330712022-12-10 A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives Gill, Muhammad Shoaib Ali Azzman, Nursyuhada Hassan, Sharifah Syed Shah, Syed Adnan Ali Ahemad, Nafees BMC Chem Research Quinolone is a privileged scaffold in medicinal chemistry and 4-Quinolone-3-Carboxamides have been reported to harbor vast therapeutic potential. However, conversion of N-1 substituted 4-Quinolone 3-Carboxylate to its corresponding carbamates is highly restrictive. This motivated us to adopt a much simpler, scalable and efficient methodology for the synthesis of highly pure N-1 substituted 4- Quinolone-3-Carboxamides with excellent yields. Our adopted methodology not only provides a robust pathway for the convenient synthesis of N-1 substituted 4- Quinolone-3-Carboxamides which can then be explored for their therapeutic potential, this may also be adaptable for the derivatization of other such less reactive carboxylate species. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s13065-022-00902-1. Springer International Publishing 2022-12-08 /pmc/articles/PMC9733071/ /pubmed/36482476 http://dx.doi.org/10.1186/s13065-022-00902-1 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/ (https://creativecommons.org/publicdomain/zero/1.0/) ) applies to the data made available in this article, unless otherwise stated in a credit line to the data.
spellingShingle Research
Gill, Muhammad Shoaib Ali
Azzman, Nursyuhada
Hassan, Sharifah Syed
Shah, Syed Adnan Ali
Ahemad, Nafees
A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives
title A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives
title_full A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives
title_fullStr A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives
title_full_unstemmed A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives
title_short A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives
title_sort green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives
topic Research
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9733071/
https://www.ncbi.nlm.nih.gov/pubmed/36482476
http://dx.doi.org/10.1186/s13065-022-00902-1
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