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Molecules 2017, 22(4), 605; doi:10.3390/molecules22040605

An Efficient One-Pot Protocol for the Synthesis of Substituted 3,4-Dihydropyrimidin-2(1H)-ones Using Metallophthalocyanines (MPcs) as Potent Heterogeneous Catalysts: Synthesis, Characterization, Aggregation and Antimicrobial Activity

1
Research Laboratory of Environmental Sciences and Technologies (LR16ES09), Higher Institute of Environmental Sciences and Technology, University of Carthage, Hammam-Lif 2050, Tunisia
2
Chemistry Department, College of Science and Arts, Qassim University, Al-Rass 51921, Saudi Arabia
3
Zoology Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
4
Área de Química Inorgánica-CIESOL, Universidad de Almería, 04120, Almería, Spain
*
Author to whom correspondence should be addressed.
Academic Editors: Diego Muñoz-Torrero, Rodolfo Lavilla and Christopher Hulme
Received: 3 February 2017 / Revised: 15 March 2017 / Accepted: 23 March 2017 / Published: 9 April 2017
(This article belongs to the Special Issue Multicomponent Reaction-Based Synthesis of Bioactive Molecules)
View Full-Text   |   Download PDF [2289 KB, uploaded 9 April 2017]   |  

Abstract

In this study, novel phthalonitrile 3 and their corresponding metal-free 4 and metallophthalocyanine derivatives 57 bearing 2-isopropenyl-4-methoxy-1-methylbenzene groups were synthesized and characterized. 3,4-Dihydropyrimidinones have been synthesized by a modified Biginelli-type reaction with various metallophthalocyanines 57 as catalysts. Compared to the classical Biginielli reaction, the new method has the advantages of good yield and short reaction time. Among the various metallophthalocyanines studied, cobalt (II)-phthalocyanine was found to be most active for this transformation. The newly prepared compounds were characterized using elemental analyses, MS, IR, 1H/13C-NMR and UV-Vis spectroscopy. In addition; the 3,4-dihydropyrimidinones (DHPMs) 812 were investigated for antimicrobial activities and revealed good activity. The minimum inhibitory concentration (MIC) was determined by the microdilution technique in Mueller-Hinton broth. The MICs were recorded after 24 hours of incubation at 37 °C. These results are promising, showing these compounds are biologically active. View Full-Text
Keywords: Biginelli reaction; dihydropyrimidinones; metallophthalocyanine derivatives; aggregation; antimicrobial activity Biginelli reaction; dihydropyrimidinones; metallophthalocyanine derivatives; aggregation; antimicrobial activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Hamdi, N.; Medyouni, R.; Bilel, H.; Mansour, L.; Romerosa, A. An Efficient One-Pot Protocol for the Synthesis of Substituted 3,4-Dihydropyrimidin-2(1H)-ones Using Metallophthalocyanines (MPcs) as Potent Heterogeneous Catalysts: Synthesis, Characterization, Aggregation and Antimicrobial Activity. Molecules 2017, 22, 605.

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