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Synthesis of Imidazo[1,2-f]phenanthridines by Recyclable Magnetic MOF-Catalyzed Coupling and Cyclization of 2-(2-Bromoaryl)imidazoles with Cyclohexane-1,3-diones Followed by Aromatization
[Image: see text] 2-(2-Bromoaryl)imidazoles react with cyclohexane-1,3-diones in the presence of a catalytic amount of recyclable Fe(3)O(4)@SiO(2)@MOF-199 and a base to give the corresponding C–C coupled and cyclized products 6,7-dihydroimidazo[1,2-f]phenanthridin-8(5H)-ones in high yields. The magn...
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/PMC9178716/ https://www.ncbi.nlm.nih.gov/pubmed/35694479 http://dx.doi.org/10.1021/acsomega.2c01038 |
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author | Lee, Seong Weon Dao, Pham Duy Quang Lim, Ho-Jin Cho, Chan Sik |
author_facet | Lee, Seong Weon Dao, Pham Duy Quang Lim, Ho-Jin Cho, Chan Sik |
author_sort | Lee, Seong Weon |
collection | PubMed |
description | [Image: see text] 2-(2-Bromoaryl)imidazoles react with cyclohexane-1,3-diones in the presence of a catalytic amount of recyclable Fe(3)O(4)@SiO(2)@MOF-199 and a base to give the corresponding C–C coupled and cyclized products 6,7-dihydroimidazo[1,2-f]phenanthridin-8(5H)-ones in high yields. The magnetic MOF catalyst could be easily recovered and reused four times without any significant loss of catalytic activity. The coupled and cyclized scaffolds were aromatized to imidazo[1,2-f]phenanthridines in high yields by a one-pot sequential procedure including reduction, dehydration, and oxidation. The present protocol could be applied to the synthesis of Zephycandidine A, which is known to exhibit anti-tumor activity. |
format | Online Article Text |
id | pubmed-9178716 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-91787162022-06-10 Synthesis of Imidazo[1,2-f]phenanthridines by Recyclable Magnetic MOF-Catalyzed Coupling and Cyclization of 2-(2-Bromoaryl)imidazoles with Cyclohexane-1,3-diones Followed by Aromatization Lee, Seong Weon Dao, Pham Duy Quang Lim, Ho-Jin Cho, Chan Sik ACS Omega [Image: see text] 2-(2-Bromoaryl)imidazoles react with cyclohexane-1,3-diones in the presence of a catalytic amount of recyclable Fe(3)O(4)@SiO(2)@MOF-199 and a base to give the corresponding C–C coupled and cyclized products 6,7-dihydroimidazo[1,2-f]phenanthridin-8(5H)-ones in high yields. The magnetic MOF catalyst could be easily recovered and reused four times without any significant loss of catalytic activity. The coupled and cyclized scaffolds were aromatized to imidazo[1,2-f]phenanthridines in high yields by a one-pot sequential procedure including reduction, dehydration, and oxidation. The present protocol could be applied to the synthesis of Zephycandidine A, which is known to exhibit anti-tumor activity. American Chemical Society 2022-05-24 /pmc/articles/PMC9178716/ /pubmed/35694479 http://dx.doi.org/10.1021/acsomega.2c01038 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 | Lee, Seong Weon Dao, Pham Duy Quang Lim, Ho-Jin Cho, Chan Sik Synthesis of Imidazo[1,2-f]phenanthridines by Recyclable Magnetic MOF-Catalyzed Coupling and Cyclization of 2-(2-Bromoaryl)imidazoles with Cyclohexane-1,3-diones Followed by Aromatization |
title | Synthesis of Imidazo[1,2-f]phenanthridines
by Recyclable Magnetic MOF-Catalyzed Coupling and
Cyclization of 2-(2-Bromoaryl)imidazoles with Cyclohexane-1,3-diones
Followed by Aromatization |
title_full | Synthesis of Imidazo[1,2-f]phenanthridines
by Recyclable Magnetic MOF-Catalyzed Coupling and
Cyclization of 2-(2-Bromoaryl)imidazoles with Cyclohexane-1,3-diones
Followed by Aromatization |
title_fullStr | Synthesis of Imidazo[1,2-f]phenanthridines
by Recyclable Magnetic MOF-Catalyzed Coupling and
Cyclization of 2-(2-Bromoaryl)imidazoles with Cyclohexane-1,3-diones
Followed by Aromatization |
title_full_unstemmed | Synthesis of Imidazo[1,2-f]phenanthridines
by Recyclable Magnetic MOF-Catalyzed Coupling and
Cyclization of 2-(2-Bromoaryl)imidazoles with Cyclohexane-1,3-diones
Followed by Aromatization |
title_short | Synthesis of Imidazo[1,2-f]phenanthridines
by Recyclable Magnetic MOF-Catalyzed Coupling and
Cyclization of 2-(2-Bromoaryl)imidazoles with Cyclohexane-1,3-diones
Followed by Aromatization |
title_sort | synthesis of imidazo[1,2-f]phenanthridines
by recyclable magnetic mof-catalyzed coupling and
cyclization of 2-(2-bromoaryl)imidazoles with cyclohexane-1,3-diones
followed by aromatization |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9178716/ https://www.ncbi.nlm.nih.gov/pubmed/35694479 http://dx.doi.org/10.1021/acsomega.2c01038 |
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