Sulfonated organic heteropolyacid salts as a highly efficient and green solid catalysts for the synthesis of 1,8-dioxo-decahydroacridine derivatives in water

AbstractIn the present study, we introduce two nonconventional ionic liquids [MIMPS]3PW12O40 (a) and [TEAPS]3PW12O40 (b) as green and highly efficient solid acid catalysts for the synthesis of 1,8-dioxo-decahydroacridine derivatives. The one-pot three component reaction of 1,3-cyclohexanediones, aromatic aldehydes and aromatic amines or ammonium acetate in water afforded the corresponding 1,8-dioxo-decahydroacridines in excellent yields. This reaction has been carried out in the presence of 1mol% of catalysts at room temperature. The reusability of the catalysts was demonstrated by a five-run test. Additionally, the catalysts pose several advantages including mild reaction conditions, cleaner reactions and shorter reaction times

1H-imidazol-3-ium tricyanomethanide {[HIM]C(CN)3} as a nanostructured molten salt catalyst: application to the synthesis of pyrano[4,3‐b]pyrans

In this work, we have synthesized a novel nanostructured molten salt, 1H-imidazol-3-ium tricyanomethanide {[HIMI]C(CN)3} (1), as an efficient and green protocol-compatible catalyst. This new molten salt has been fully characterized by different analytical techniques, such as FT-IR, 1HNMR, 13CNMR, thermal gravimetric analysis, derivative thermal gravimetric analysis, differential thermal analysis, X-ray diffraction, scanning electron microscopy, and high-resolution transmission electron microscopy. Additionally, the catalytic activity of {[HIMI]C(CN)3} (1, 2 mol%) has been tested in a three-component domino Knoevenagel condensation reaction. A range of structurally diverse aromatic aldehydes (2a–p), malononitrile (3), and 4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one (4) are tolerated for the synthesis of 2-amino-7-methyl-5-oxo-4-aryl-4,5-dihydropyrano[4,3-b]pyran-3-carbonitrile derivatives (5a–p) under neat conditions at 50 °C. The obtained results have demonstrated that catalyst 1 shows interesting catalytic properties, such as clean reaction profile, cost-effectiveness, and green conditions. Importantly, the aforementioned catalyst is thermally stable with a 171 °C melting point not showing any significant loss in catalytic activity after 7 reaction cycles.We thank Bu-Ali Sina University, Iran National Science Foundation (INSF) (Grant of Allameh Tabataba’i’s Award, Grant Number BN093), National Elites Foundation, University of Alicante (VIGROB-173), and the Spanish Ministerio de Economíay Competitividad (CTQ2015-66624-P) for financial support to our research groups

Novel nano molten salt tetra-2,3-pyridiniumporphyrazinato-oxo-vanadium tricyanomethanide as a vanadium surface-free phthalocyanine catalyst: Application to Strecker synthesis of α-aminonitrile derivatives

Efficient and recyclable novel nano tetra-2,3-pyridiniumporphyrazinato-oxo-vanadium tricyanomethanide, {[VO(TPPA)][C(CN)3]4}, as a vanadium surface-free phthalocyanine-based molten salt catalyst was successfully designed, produced and used for the Strecker synthesis of α-aminonitrile derivatives through a one-pot three-component reaction between aromatic aldehydes, trimethylsilyl cyanide and aniline derivatives under neat conditions at 50 °C. This catalyst was well characterized using Fourier transform infrared, UV–visible, X-ray photoelectron and energy-dispersive X-ray spectroscopies, X-ray diffraction, scanning and high-resolution transmission electron microscopies, inductively coupled plasma mass spectrometry and thermogravimetric analysis. The catalyst can be simply recovered and reused several times without significant loss of catalytic activity.We thank Bu‐Ali Sina University, Nahavand University, the Iran National Science Foundation (INSF, grant no. 95820271), the National Elites Foundation, the University of Alicante (VIGROB‐173) and the Spanish Ministerio de Economíay Competitividad (CTQ2015‐66624‐P) for financial support to our research groups

Synthesis and application of chitosan supported vanadium oxo in the synthesis of 1,4-dihydropyridines and 2,4,6-triarylpyridines via anomeric based oxidation

Chitosan, as a biopolymer, exhibits a strong affinity for complexation with suitable metal ions. Thus, it has received increased attention for the preparation of stable bioorganic–inorganic hybrid heterogeneous catalysts. Herein, a novel chitosan based vanadium oxo (ChVO) catalyst was prepared and fully characterized by several techniques such as Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), derivative thermal gravimetric (DTG), differential thermal analysis (DTA), scanning electron microscopy (SEM), energy dispersive X-ray analysis (EDX), high-resolution transmission electron microscopy (HRTEM), selected area electron diffraction (SAED), X-ray photoelectron spectroscopy (XPS) and inductively coupled plasma mass spectrometry (ICP-MS). The synthesized catalyst has been successfully used as a reusable catalyst in the synthesis of dihydropyridines and triarylpyridines.We thank Bu-Ali Sina University, Nahavand University, the Iran National Science Foundation (INSF) (Grant No: 95831207) and the National Elites Foundation for financial support of our research group

Design, synthesis, and application of 1H-imidazol-3-ium trinitromethanide {[HIMI]C(NO2)3} as a recyclable nanostructured ionic liquid (NIL) catalyst for the synthesis of imidazo[1,2-a]pyrimidine-3-carbonitriles

In this study, 1H-imidazol-3-ium trinitromethanide (1) {[HIMI]C(NO2)3} as a green and recyclable catalyst based on nanostructure ionic liquid (NIL) was designed, synthesized, fully characterized by various analysis techniques, and applied as catalyst for the synthesis of 4-amino-1,2-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carbonitrile derivatives via one-pot three-component condensation reaction. The reaction tolerates a wide range of electron-donating and electron-withdrawing substituents on aldehydes with malononitrile and 2-aminobenzimidazole at 50 °C under neat conditions. The described reaction is compatible with the green chemistry disciplines and their main advantages are short reaction time, high yields, simplicity of product isolation, and clean reaction profile. Additionally, the NIL catalyst (1) {[HIMI]C(NO2)3} can be readily recovered in the reaction vessel using a mixture of EtOAc/H2O (1:1) and reused for four consecutive runs without a significant loss in catalytic activity. The present study can open up a new and promising insight in the course of rational design, synthesis and applications of nanostructured task-specific ionic liquids (NTSILs) for numerous green purposes.We thank Bu-Ali Sina University, Iran National Science Foundation (INSF) (Grant number: 940124), National Elites Foundation, University of Alicante (VIGROB-173), and the Spanish Ministerio de Economía y Competitividad (CTQ2015-66624-P) for financial support to our research groups

Design and preparation of [4,4′-bipyridine]-1,1′-diium trinitromethanide (BPDTNM) as a novel nanosized ionic liquid catalyst: application to the synthesis of 1-(benzoimidazolylamino)methyl-2-naphthols

In this work, the novel bifunctional nanosized ionic liquid catalyst [4,4′-bipyridine]-1,1′-diium trinitromethanide (BPDTNM) was designed, synthesized, and characterized by using FT-IR spectra, 1H and 13C NMR spectra, X-ray diffraction patterns (XRD), scanning electron microscopy (SEM), high resolution transmission electron microscopy (HRTEM), thermogravimetry (TG), derivative thermogravimetry (DTG) analysis, differential thermal analysis (DTA), and HPLC-mass spectroscopy. The synthesized nanosized catalyst was successfully applied to the synthesis of 1-(benzoimidazolylamino)methyl-2-naphthol derivatives via a straightforward one-pot three-component condensation reaction of 2-aminobenzimidazole, 2-naphthol, and a wide range of aromatic aldehydes under mild and solvent-free conditions.We thank Bu-Ali Sina University, the Iran National Science Foundation (INSF) (The Grant of Allameh Tabataba’i’s Award, Grant Number: BN093), National Elites Foundation, the University of Alicante (VIGROB-173), and the Spanish Ministerio de Economía y Competitividad (CTQ2015-66624-P) for financial support to our research groups

{[1,4-DHPyrazine][C(CN)(3)](2)} as a New Nano Molten Salt Catalyst for the Synthesis of Novel Piperazine Based bis(4-hydroxy-2H-chromen-2-one) Derivatives

In this article a convenient method for the synthesis of novel piperazine based bis(4-hydroxy-2H-chromen-2-one) derivatives using pyrazine-1,4-diium tricyanomethanide {[1,4-DHPyrazine][C(CN)(3)](2)} as a new nanostructured molten salt (NMS) catalyst has been described. These compounds were synthesized via Mannich type reaction between several aromatic aldehyde, piperazine and 4-hydroxycoumarin under solvent-free condition at room temperature. The NMS catalyst was fully characterized via Fourier transform infrared (FT-IR), nuclear magnetic resonance (H-1 NMR and C-13 NMR), mass spectrometry, thermal gravimetric, derivative thermal gravimetric, differential thermal analysis, X-ray diffraction patterns, scanning electron microscopy and transmission electron microscopy analysis. The new compounds synthesized by using this NMS catalyst were also characterized by FT-IR, H-1 NMR and C-13 NMR, high-resolution mass spectrometry techniques. The new NMS catalyst simply recovers and can be reused several times without significant loss of catalytic activity. The major advantages of the described method in comparison to the classical reactions are low catalyst loading, short reaction time, high yields, simple isolation of product and reusability of the NMS catalyst. Pyrazine-1,4-diium tricyanomethanide as a nano molten salt catalyst was designed, synthesized and used for the synthesis of novel biological piperazine based bis(4-hydroxy-2H-chromen-2- one) derivatives as bioactive and drug candidates. [GRAPHICS]

Application of Triphenylammonium Tricyanomethanide as an Efficient and Recyclable Nanostructured Molten-Salt Catalyst for the Synthesis of N-Benzylidene-2-arylimidazo[1,2-a] pyridin-3-amines

Triphenylammonium tricyanomethanide (Ph3NH)[C(CN)3] was synthesized and used as an efficient and recyclable nanostructured molten-salt (NMS) catalyst for the synthesis of N-benzylidene-2-arylimidazo[1,2-a] pyridin-3-amines by the reaction of various (het) aryl aldehydes with trimethylsilyl cyanide and pyridin-2-amine under solvent-free conditions at 50 degrees C. The NMS catalyst could be simply recycled and reused several times without significant loss of its catalytic activity

Catalytic application of a nano-molten salt catalyst in the synthesis of biological naphthoquinone-based compounds

In this investigation, a new application of 1H-imidazol-3-ium tricyanomethanide catalyst was explored. The catalyst presented a robust catalytic applicability for the preparation of naphthoquinone-based compounds under mild and green reaction conditions. A wide range of aromatic aldehydes were able to react with 2-hydroxynaphthalene-1,4-dione and 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one or malononitrile to afford the desired naphthoquinone-based molecules in short time with high to excellent yields.We thank Bu-Ali Sina University and the Iran National Science Foundation (INSF) for financial support (grant no. 940124), and Iran’s National Elites Foundation for recognizing our research group