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Recyclable Magnetic Cu-MOF-74-Catalyzed C(sp(2))-N Coupling and Cyclization under Microwave Irradiation: Synthesis of Imidazo[1,2-c]quinazolines and Their Analogues

[Image: see text] Magnetic Cu-MOF-74 (Fe(3)O(4)@SiO(2)@Cu-MOF-74) was synthesized for the first time by grafting MOF-74 (copper as the metal center) on the surface of core-shell magnetic carboxyl-functionalized silica gel (Fe(3)O(4)@SiO(2)-COOH), which was prepared by coating core Fe(3)O(4) nanopart...

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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 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10173347/
https://www.ncbi.nlm.nih.gov/pubmed/37179653
http://dx.doi.org/10.1021/acsomega.3c00680
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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] Magnetic Cu-MOF-74 (Fe(3)O(4)@SiO(2)@Cu-MOF-74) was synthesized for the first time by grafting MOF-74 (copper as the metal center) on the surface of core-shell magnetic carboxyl-functionalized silica gel (Fe(3)O(4)@SiO(2)-COOH), which was prepared by coating core Fe(3)O(4) nanoparticles with hydrolyzed 2-(3-(triethoxysilyl)propyl)succinic anhydride and tetraethyl orthosilicate. The structure of Fe(3)O(4)@SiO(2)@Cu-MOF-74 nanoparticles was characterized by Fourier transform infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDS), and transmission electron microscopy (TEM). The prepared Fe(3)O(4)@SiO(2)@Cu-MOF-74 nanoparticles could be applied as a recyclable catalyst to the synthesis of N-fused hybrid scaffolds. 2-(2-Bromoaryl)imidazoles and 2-(2-bromovinyl)imidazoles were coupled and cyclized with cyanamide in DMF in the presence of a catalytic amount of Fe(3)O(4)@SiO(2)@Cu-MOF-74 along with a base to give imidazo[1,2-c]quinazolines and imidazo[1,2-c]pyrimidines, respectively, in good yields. The Fe(3)O(4)@SiO(2)@Cu-MOF-74 catalyst could be easily recovered by a super magnetic bar and recycled more than four times while almost maintaining catalytic activity.
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spelling pubmed-101733472023-05-12 Recyclable Magnetic Cu-MOF-74-Catalyzed C(sp(2))-N Coupling and Cyclization under Microwave Irradiation: Synthesis of Imidazo[1,2-c]quinazolines and Their Analogues Lee, Seong Weon Dao, Pham Duy Quang Lim, Ho-Jin Cho, Chan Sik ACS Omega [Image: see text] Magnetic Cu-MOF-74 (Fe(3)O(4)@SiO(2)@Cu-MOF-74) was synthesized for the first time by grafting MOF-74 (copper as the metal center) on the surface of core-shell magnetic carboxyl-functionalized silica gel (Fe(3)O(4)@SiO(2)-COOH), which was prepared by coating core Fe(3)O(4) nanoparticles with hydrolyzed 2-(3-(triethoxysilyl)propyl)succinic anhydride and tetraethyl orthosilicate. The structure of Fe(3)O(4)@SiO(2)@Cu-MOF-74 nanoparticles was characterized by Fourier transform infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDS), and transmission electron microscopy (TEM). The prepared Fe(3)O(4)@SiO(2)@Cu-MOF-74 nanoparticles could be applied as a recyclable catalyst to the synthesis of N-fused hybrid scaffolds. 2-(2-Bromoaryl)imidazoles and 2-(2-bromovinyl)imidazoles were coupled and cyclized with cyanamide in DMF in the presence of a catalytic amount of Fe(3)O(4)@SiO(2)@Cu-MOF-74 along with a base to give imidazo[1,2-c]quinazolines and imidazo[1,2-c]pyrimidines, respectively, in good yields. The Fe(3)O(4)@SiO(2)@Cu-MOF-74 catalyst could be easily recovered by a super magnetic bar and recycled more than four times while almost maintaining catalytic activity. American Chemical Society 2023-04-25 /pmc/articles/PMC10173347/ /pubmed/37179653 http://dx.doi.org/10.1021/acsomega.3c00680 Text en © 2023 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
Recyclable Magnetic Cu-MOF-74-Catalyzed C(sp(2))-N Coupling and Cyclization under Microwave Irradiation: Synthesis of Imidazo[1,2-c]quinazolines and Their Analogues
title Recyclable Magnetic Cu-MOF-74-Catalyzed C(sp(2))-N Coupling and Cyclization under Microwave Irradiation: Synthesis of Imidazo[1,2-c]quinazolines and Their Analogues
title_full Recyclable Magnetic Cu-MOF-74-Catalyzed C(sp(2))-N Coupling and Cyclization under Microwave Irradiation: Synthesis of Imidazo[1,2-c]quinazolines and Their Analogues
title_fullStr Recyclable Magnetic Cu-MOF-74-Catalyzed C(sp(2))-N Coupling and Cyclization under Microwave Irradiation: Synthesis of Imidazo[1,2-c]quinazolines and Their Analogues
title_full_unstemmed Recyclable Magnetic Cu-MOF-74-Catalyzed C(sp(2))-N Coupling and Cyclization under Microwave Irradiation: Synthesis of Imidazo[1,2-c]quinazolines and Their Analogues
title_short Recyclable Magnetic Cu-MOF-74-Catalyzed C(sp(2))-N Coupling and Cyclization under Microwave Irradiation: Synthesis of Imidazo[1,2-c]quinazolines and Their Analogues
title_sort recyclable magnetic cu-mof-74-catalyzed c(sp(2))-n coupling and cyclization under microwave irradiation: synthesis of imidazo[1,2-c]quinazolines and their analogues
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10173347/
https://www.ncbi.nlm.nih.gov/pubmed/37179653
http://dx.doi.org/10.1021/acsomega.3c00680
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