Cargando…

Deep Eutectic Solvent (DES)-Mediated One-Pot Multicomponent Green Approach for Naphthalimide-Centered Acridine-1,8-dione Derivatives and Their Photophysical Properties

[Image: see text] An efficient and green methodology to assemble various functionalized naphthalimide-centered acridine-1,8-dione derivatives involving a one-pot multicomponent protocol has successfully been developed. Herein, a variety of aromatic aldehydes, 1,3-diketones, 1,8-naphthanoic anhydride...

Descripción completa

Detalles Bibliográficos
Autores principales: Rather, Ishfaq Ahmad, Alotaibi, Saad H., Alotaibi, Mohammed T., Altaf, Mohammad, Ali, Rashid
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9558244/
https://www.ncbi.nlm.nih.gov/pubmed/36249394
http://dx.doi.org/10.1021/acsomega.2c04026
_version_ 1784807397102977024
author Rather, Ishfaq Ahmad
Alotaibi, Saad H.
Alotaibi, Mohammed T.
Altaf, Mohammad
Ali, Rashid
author_facet Rather, Ishfaq Ahmad
Alotaibi, Saad H.
Alotaibi, Mohammed T.
Altaf, Mohammad
Ali, Rashid
author_sort Rather, Ishfaq Ahmad
collection PubMed
description [Image: see text] An efficient and green methodology to assemble various functionalized naphthalimide-centered acridine-1,8-dione derivatives involving a one-pot multicomponent protocol has successfully been developed. Herein, a variety of aromatic aldehydes, 1,3-diketones, 1,8-naphthanoic anhydride, and hydrazine hydrate have been condensed under a reusable, inexpensive, and biodegradable deep eutectic solvent (DES) of N,N′-dimethyl urea and l-(+)-tartaric acid to obtain the desired targets under operationally mild reaction conditions with outstanding conversions. Strikingly, in this strategy, the DES plays a dual role of a catalyst and solvent and was recycled efficiently in four consecutive runs with no substantial drop in the yield of the desired product. Interestingly, the easy recovery and high reusability of the DES make this simple yet efficient protocol environmentally desirable. Moreover, the preliminary photophysical properties of thus-prepared valuable molecules have also been investigated by ultraviolet–visible (UV–vis) and fluorescence spectroscopy.
format Online
Article
Text
id pubmed-9558244
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-95582442022-10-14 Deep Eutectic Solvent (DES)-Mediated One-Pot Multicomponent Green Approach for Naphthalimide-Centered Acridine-1,8-dione Derivatives and Their Photophysical Properties Rather, Ishfaq Ahmad Alotaibi, Saad H. Alotaibi, Mohammed T. Altaf, Mohammad Ali, Rashid ACS Omega [Image: see text] An efficient and green methodology to assemble various functionalized naphthalimide-centered acridine-1,8-dione derivatives involving a one-pot multicomponent protocol has successfully been developed. Herein, a variety of aromatic aldehydes, 1,3-diketones, 1,8-naphthanoic anhydride, and hydrazine hydrate have been condensed under a reusable, inexpensive, and biodegradable deep eutectic solvent (DES) of N,N′-dimethyl urea and l-(+)-tartaric acid to obtain the desired targets under operationally mild reaction conditions with outstanding conversions. Strikingly, in this strategy, the DES plays a dual role of a catalyst and solvent and was recycled efficiently in four consecutive runs with no substantial drop in the yield of the desired product. Interestingly, the easy recovery and high reusability of the DES make this simple yet efficient protocol environmentally desirable. Moreover, the preliminary photophysical properties of thus-prepared valuable molecules have also been investigated by ultraviolet–visible (UV–vis) and fluorescence spectroscopy. American Chemical Society 2022-09-26 /pmc/articles/PMC9558244/ /pubmed/36249394 http://dx.doi.org/10.1021/acsomega.2c04026 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Rather, Ishfaq Ahmad
Alotaibi, Saad H.
Alotaibi, Mohammed T.
Altaf, Mohammad
Ali, Rashid
Deep Eutectic Solvent (DES)-Mediated One-Pot Multicomponent Green Approach for Naphthalimide-Centered Acridine-1,8-dione Derivatives and Their Photophysical Properties
title Deep Eutectic Solvent (DES)-Mediated One-Pot Multicomponent Green Approach for Naphthalimide-Centered Acridine-1,8-dione Derivatives and Their Photophysical Properties
title_full Deep Eutectic Solvent (DES)-Mediated One-Pot Multicomponent Green Approach for Naphthalimide-Centered Acridine-1,8-dione Derivatives and Their Photophysical Properties
title_fullStr Deep Eutectic Solvent (DES)-Mediated One-Pot Multicomponent Green Approach for Naphthalimide-Centered Acridine-1,8-dione Derivatives and Their Photophysical Properties
title_full_unstemmed Deep Eutectic Solvent (DES)-Mediated One-Pot Multicomponent Green Approach for Naphthalimide-Centered Acridine-1,8-dione Derivatives and Their Photophysical Properties
title_short Deep Eutectic Solvent (DES)-Mediated One-Pot Multicomponent Green Approach for Naphthalimide-Centered Acridine-1,8-dione Derivatives and Their Photophysical Properties
title_sort deep eutectic solvent (des)-mediated one-pot multicomponent green approach for naphthalimide-centered acridine-1,8-dione derivatives and their photophysical properties
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9558244/
https://www.ncbi.nlm.nih.gov/pubmed/36249394
http://dx.doi.org/10.1021/acsomega.2c04026
work_keys_str_mv AT ratherishfaqahmad deepeutecticsolventdesmediatedonepotmulticomponentgreenapproachfornaphthalimidecenteredacridine18dionederivativesandtheirphotophysicalproperties
AT alotaibisaadh deepeutecticsolventdesmediatedonepotmulticomponentgreenapproachfornaphthalimidecenteredacridine18dionederivativesandtheirphotophysicalproperties
AT alotaibimohammedt deepeutecticsolventdesmediatedonepotmulticomponentgreenapproachfornaphthalimidecenteredacridine18dionederivativesandtheirphotophysicalproperties
AT altafmohammad deepeutecticsolventdesmediatedonepotmulticomponentgreenapproachfornaphthalimidecenteredacridine18dionederivativesandtheirphotophysicalproperties
AT alirashid deepeutecticsolventdesmediatedonepotmulticomponentgreenapproachfornaphthalimidecenteredacridine18dionederivativesandtheirphotophysicalproperties