Iron–Phosphonate Nanomaterial: As a Novel and Efficient Organic–Inorganic Hybrid Catalyst for Solvent-Free Synthesis of Tri-Substituted Imidazole Derivatives

Iron‐catalyzed intermolecular and intramolecular cyclization reactions of N‐heterocycles

“…The substrates benzaldehyde 99 , benzyl 98 , and ammonium acetate 100 were employed in the reaction along with Fe‐DTPMP (iron‐phosphonate nanostructures) [75] as a catalyst, at 100°C to produce trisubstituted imidazoles 101 . A diverse array of aromatic aldehydes interacted efficiently to produce excellent yields of 2,4,5‐trisubstituted imidazoles.…”

Metal-based catalysts containing a phosphonate moiety – from synthesis to applications in organic chemistry

“…In 2020, Arpanahi et al presented a novel organic-inorganic hybrid catalyst based on the ligand, diethylenetriamine penta(methylene phosphonic acid) (DTPMP) 29. 80 The described catalyst showed high activity in condensation reactions between aromatic aldehydes 82, 1,2-diphenyl-1,2-ethanedione 92, and ammonium acetate to 2,4,5-trisubstituted imidazoles 93 (Scheme 27 A). The authors found that the yields of the heterocyclic compounds were influenced by the substituent from the aromatic ring of the aldehyde.…”

“…After drying, the precipitated solid was characterized using a number of structural analyses, including FT-IR, TGA, XRD, BET and others. 80 For comparison, the condensation of various aromatic aldehydes 94 with o-phenylenediamine 95 using an organic-inorganic hybrid porous iron-phosphonate CAT43 gave the benzimidazole derivatives 96 in yields ranging from 30-92% (Scheme 28A). This catalyst was synthesized from hexamethylenediamine-N,N,N′,N′tetrakis-(methylphosphonic acid) 81 (HDTMP) and FeCl3 under different hydrothermal conditions (Scheme 28B), and possessed structures of nanoparticles or nanorods or flake-like morphology.…”

Pyromellitic diamide–diacid bridged mesoporous organosilica nanospheres with controllable morphologies: a novel PMO for the facile and expeditious synthesis of imidazole derivatives

“…In recent years, the synthesis of imidazole derivatives using benzoin, as a commercially available substrate, in the presence of various catalysts has been reported to a limited extent. 74 Among recent homogeneous or heterogeneous catalysts are molecular iodine, 97 Fe 3 O 4 /SiO 2 -urea nanoparticles, 98 iron–phosphonate nanomaterial, 99 poly(2-acrylamido-2-methylpropanesulfonic acid- co -acrylic acid- co -acrylamide), molecularly imprinted polymer, 100 2,6-dimethylpyridinium trinitromethanide molten salt, 78 magnetic graphitic carbon nitride, 101 graphene oxide–chitosan composite, 102 ferric( iii ) nitrate supported on kieselguhr, 103 and isocyanurate-based periodic mesoporous organosilica. 77 In spite of their merits, some of the reported methods for the synthesis of imidazole derivatives suffer from disadvantages due to the high loading of the catalyst, utilizing toxic solvents and/or expensive metal catalysts, low production yields, long reaction times as well as laborious and hard purification procedures and irreversible environmental risks.…”