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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...

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Autores principales: Lee, Seong Weon, Dao, Pham Duy Quang, Lim, Ho-Jin, Cho, Chan Sik
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
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.
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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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