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Iodine-Catalyzed Multicomponent Synthesis of Highly Fluorescent Pyrimidine-Linked Imidazopyridines

[Image: see text] Herein, we report a metal-free one-pot three-component reaction of aryl methyl ketones, 2-aminopyridines, and barbituric acids for the synthesis of pyrimidine-linked imidazopyridines using a catalytic amount of molecular iodine in DMSO medium. This process involves a one-pot C–H ox...

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Autores principales: Acharya, Swadhin Swaraj, Bhaumick, Prabhas, Kumar, Rohit, Choudhury, Lokman H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9178772/
https://www.ncbi.nlm.nih.gov/pubmed/35694517
http://dx.doi.org/10.1021/acsomega.2c01332
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author Acharya, Swadhin Swaraj
Bhaumick, Prabhas
Kumar, Rohit
Choudhury, Lokman H.
author_facet Acharya, Swadhin Swaraj
Bhaumick, Prabhas
Kumar, Rohit
Choudhury, Lokman H.
author_sort Acharya, Swadhin Swaraj
collection PubMed
description [Image: see text] Herein, we report a metal-free one-pot three-component reaction of aryl methyl ketones, 2-aminopyridines, and barbituric acids for the synthesis of pyrimidine-linked imidazopyridines using a catalytic amount of molecular iodine in DMSO medium. This process involves a one-pot C–H oxidation, followed by the formation of one C–C and two C–N bonds. A wide variety of aryl methyl ketones and 2-aminopyridines were found to be suitable for this methodology. The UV and fluorescence properties of the synthesized products were studied in water and DMSO media. Most of the synthesized products exhibited very good to excellent fluorescence quantum yield. Among all the products, compounds 4p and 4q showed the maximum fluorescence quantum yield (0.36) in water medium under basic conditions and compound 4c showed the maximum fluorescence quantum yield (0.75) in DMSO medium.
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spelling pubmed-91787722022-06-10 Iodine-Catalyzed Multicomponent Synthesis of Highly Fluorescent Pyrimidine-Linked Imidazopyridines Acharya, Swadhin Swaraj Bhaumick, Prabhas Kumar, Rohit Choudhury, Lokman H. ACS Omega [Image: see text] Herein, we report a metal-free one-pot three-component reaction of aryl methyl ketones, 2-aminopyridines, and barbituric acids for the synthesis of pyrimidine-linked imidazopyridines using a catalytic amount of molecular iodine in DMSO medium. This process involves a one-pot C–H oxidation, followed by the formation of one C–C and two C–N bonds. A wide variety of aryl methyl ketones and 2-aminopyridines were found to be suitable for this methodology. The UV and fluorescence properties of the synthesized products were studied in water and DMSO media. Most of the synthesized products exhibited very good to excellent fluorescence quantum yield. Among all the products, compounds 4p and 4q showed the maximum fluorescence quantum yield (0.36) in water medium under basic conditions and compound 4c showed the maximum fluorescence quantum yield (0.75) in DMSO medium. American Chemical Society 2022-05-25 /pmc/articles/PMC9178772/ /pubmed/35694517 http://dx.doi.org/10.1021/acsomega.2c01332 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 Acharya, Swadhin Swaraj
Bhaumick, Prabhas
Kumar, Rohit
Choudhury, Lokman H.
Iodine-Catalyzed Multicomponent Synthesis of Highly Fluorescent Pyrimidine-Linked Imidazopyridines
title Iodine-Catalyzed Multicomponent Synthesis of Highly Fluorescent Pyrimidine-Linked Imidazopyridines
title_full Iodine-Catalyzed Multicomponent Synthesis of Highly Fluorescent Pyrimidine-Linked Imidazopyridines
title_fullStr Iodine-Catalyzed Multicomponent Synthesis of Highly Fluorescent Pyrimidine-Linked Imidazopyridines
title_full_unstemmed Iodine-Catalyzed Multicomponent Synthesis of Highly Fluorescent Pyrimidine-Linked Imidazopyridines
title_short Iodine-Catalyzed Multicomponent Synthesis of Highly Fluorescent Pyrimidine-Linked Imidazopyridines
title_sort iodine-catalyzed multicomponent synthesis of highly fluorescent pyrimidine-linked imidazopyridines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9178772/
https://www.ncbi.nlm.nih.gov/pubmed/35694517
http://dx.doi.org/10.1021/acsomega.2c01332
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