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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Published in:BMC Chemistry
Main Author: Gill M.S.A.; Azzman N.; Hassan S.S.; Shah S.A.A.; Ahemad N.
Format: Article
Language:English
Published: BioMed Central Ltd 2022
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85143620076&doi=10.1186%2fs13065-022-00902-1&partnerID=40&md5=5d44f2e69f37a35f13c17bc0b718d7a0
id 2-s2.0-85143620076
spelling 2-s2.0-85143620076
Gill M.S.A.; Azzman N.; Hassan S.S.; Shah S.A.A.; Ahemad N.
A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives
2022
BMC Chemistry
16
1
10.1186/s13065-022-00902-1
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85143620076&doi=10.1186%2fs13065-022-00902-1&partnerID=40&md5=5d44f2e69f37a35f13c17bc0b718d7a0
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. © 2022, The Author(s).
BioMed Central Ltd
2661801X
English
Article
All Open Access; Gold Open Access
author Gill M.S.A.; Azzman N.; Hassan S.S.; Shah S.A.A.; Ahemad N.
spellingShingle Gill M.S.A.; Azzman N.; Hassan S.S.; Shah S.A.A.; Ahemad N.
A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives
author_facet Gill M.S.A.; Azzman N.; Hassan S.S.; Shah S.A.A.; Ahemad N.
author_sort Gill M.S.A.; Azzman N.; Hassan S.S.; Shah S.A.A.; Ahemad N.
title 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_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_sort A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives
publishDate 2022
container_title BMC Chemistry
container_volume 16
container_issue 1
doi_str_mv 10.1186/s13065-022-00902-1
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85143620076&doi=10.1186%2fs13065-022-00902-1&partnerID=40&md5=5d44f2e69f37a35f13c17bc0b718d7a0
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. © 2022, The Author(s).
publisher BioMed Central Ltd
issn 2661801X
language English
format Article
accesstype All Open Access; Gold Open Access
record_format scopus
collection Scopus
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