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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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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. |
format | Online Article Text |
id | pubmed-9178772 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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