journal article·2022-05-28Open access

Nanostructured Na2CaP2O7: A New and Efficient Catalyst for One-Pot Synthesis of 2-Amino-3-Cyanopyridine Derivatives and Evaluation of Their Antibacterial Activity

Redouane Achagar, Abdelhakim Elmakssoudi, Abderrahmane Thoume, Mohamed Dakir, Abdelaziz Elamrani, Yassine Zouheir, Mohamed Zahouily, Zouhair Ait-Touchente, Jamal Jamaleddine, Mohamed M. Chehimi

Applied Sciences· Volume 12· Issue 11

Abstract

A facile and novel synthesis of thirteen 2-amino-3-cyanopyridine derivatives 5(a–m) by a one-pot multicomponent reactions (MCRs) is described for the first time, starting from aromatic aldehydes, malononitrile, methyl ketones, or cyclohexanone and ammonium acetate in the presence of the nanostructured diphosphate Na2CaP2O7 (DIPH) at 80 °C under solvent-free conditions. These compounds were brought into existence in a short period with good to outstanding yields (84–94%). The diphosphate Na2CaP2O7 was synthesized and characterized by different techniques (FT-IR, XRD, SEM, and TEM) and used as an efficient, environmentally friendly, easy-to-handle, harmless, secure, and reusable catalyst. Our study was strengthened by combining five new pyrido[2,3-d]pyrimidine derivatives 6(b, c, g, h, j) by intermolecular cyclization of 2-amino-3-cyanopyridines 5(b, c, g, h, j) with formamide. The synthesized products were characterized by FT-IR, 1H NMR, and 13C NMR and by comparing measured melting points with known values reported in the literature. Gas chromatography/mass spectrometry was used to characterize the newly synthesized products and evaluate their purity. The operating conditions were optimized using a model reaction in which the catalyst amount, temperature, time, and solvent effect were evaluated. Antibacterial activity was tested against approved Gram-positive and Gram-negative strains for previously mentioned compounds.
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Research context

OpenAlex topics: Multicomponent Synthesis of Heterocycles · Synthesis and biological activity · Phenothiazines and Benzothiazines Synthesis and Activities

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Laboratory of Organic Synthesis, Extraction, and Valorization, FSAC, Hassan II University of Casablanca, B.P. 2693 Maarif, Casablanca 20000, Morocco

Laboratory of Molecular Bacteriology, Pasteur Institute of Morocco, Casablanca 20250, Morocco

Laboratory for Materials, Catalysis and Valorization of Natural Resources, Faculty of Sciences and Technology, Hassan II University of Casablanca, Mohammedia 28806, Morocco

Laboratory of Applied Chemistry & Environment, Université Mohammed Premier, Oujda 60000, Morocco

Interfaces, Traitements, Organisation et Dynamique des Systèmes (ITODYS), CNRS-UMR 7086, Université Paris Cité, F-75013 Paris, France

Funding

National Center for Scientific and Technical Research (CNRST) · University Hassan II of Casablanca · Molecular Bacteriology Laboratory, Pasteur Institute, Casablanca

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