103183-96-6Relevant academic research and scientific papers
Hantzsch reaction on free nano-Fe2O3 catalyst: Excellent reactivity combined with facile catalyst recovery and recyclability
Koukabi, Nadiya,Kolvari, Eskandar,Khazaei, Ardeshir,Zolfigol, Mohammad Ali,Shirmardi-Shaghasemi, Behzad,Khavasi, Hamid Reza
, p. 9230 - 9232 (2011)
A magnetic nanoparticle catalyst was readily prepared from inexpensive starting materials which catalyzed the Hantzsch reaction. High catalytic activity and ease of recovery from the reaction mixture using an external magnet, and several reuse times without significant losses in performance are additional eco-friendly attributes of this catalytic system.
Synthesis of substituted 1,4-dihydropyridines in water using phase-transfer catalyst under microwave irradiation
Salehi, Hojatollah,Guo, Qing-Xiang
, p. 4349 - 4357 (2004)
The synthesis of various substituted 1,4-dihydropyridines has been achieved by the reaction of aldehydes, ethyl/methyl acetoacetates, and ammonium acetate in water using phase-transfer catalyst under microwave irradiation. Compared to the classical Hantzsch's reaction conditions, this new method consistently has the advantage of good yields and short reaction times. Bifunctional compounds containing two units have been synthesized using dialdehyde as precursor in good yields.
Sulfonic acid-functionalized silica: A remarkably efficient heterogeneous reusable catalyst for the one-pot synthesis of 1, 4-dihydropyridines
Mohammadi, Behzad,Hosseini Jamkarani, Sayyed Mohammad,Kamali, Taghi A.,Nasrollahzadeh, Mahmoud,Mohajeri, Ali
, p. 613 - 619 (2010)
An efficient one-pot method for the synthesis of 1, 4-dihydropyridines from β-dicarbonyl compounds, aldehyde, and ammonium acetate is reported using sulfonic acid-functionalized silica at 90 ° C under solvent-free conditions with good to excellent yields. The catalyst is easily prepared, stable (up to 300 ° C), reusable, and efficiently used under reaction conditions. tuebitak.
Microwave-assisted oxidative aromatization of Hantzsch 1,4-dihydropyridines using manganese dioxide
Bagley, Mark C.,Lubinu, M. Caterina
, p. 1283 - 1288 (2006)
4-Aryl- and 4-alkyl-1,4-dihydropyridines, prepared by microwave-assisted Hantzsch reaction, are readily and efficiently aromatized in only one minute using commercial manganese dioxide in the absence of an inorganic support at 100 °C under microwave irradiation. This rapid procedure is more efficient than microwave-assisted aromatization using Pd/C, iodine or o-iodoxybenzoic acid (IBX) and gives the dehydrogenated or 4-dealkylated product in 91-100% yield (13 examples). Georg Thieme Verlag Stuttgart.
Adducts of diketene, alcohols, and aldehydes: Useful building blocks for 3,4-dihydropyrimidinones and 1,4-dihydropyridines
Alizadeh, Abdolali,Rostamnia, Sadegh
, p. 4057 - 4060 (2010)
A novel, one-pot, solvent-free synthesis of 3,4-dihydropyrimidin-2-(1H)-one and 1,4-dihydropyridines derivatives via a four-component cyclocondensation reaction of diketene, alcohol, and aldehyde with urea or ammonium acetate is presented. Georg Thieme Ve
LiBr as an efficient catalyst for one-pot synthesis of Hantzsch 1,4-dihydropyridines under mild conditions
Yadav,Patel,Srivastava,Watal,Yadav
, p. 118 - 122 (2011)
A simple, inexpensive and efficient one-pot synthesis of 1,4-dihydropyridines has been accomplished via lithium bromide-catalyzed Hantzsch three-component condensation reaction of an aldehyde, αβ-ketoester and ammonium acetate in acetonitrile at room temperature in good to excellent yields. The present protocol is applicable to wide range of substrates including aliphatic, aromatic and heterocyclic aldehydes affording 1,4-dihydropyridines. A simple, inexpensive and efficient one-pot synthesis of 1,4-dihydropyridines has been accomplished via lithium bromide-catalyzed Hantzsch three-component condensation reaction of an aldehyde, αβ-ketoester and ammonium acetate in acetonitrile at room temperature in good to excellent yields. The present protocol is applicable to wide range of substrates including aliphatic, aromatic and heterocyclic aldehydes affording 1,4-dihydropyridines. Copyright
Ultrasound-accelerated synthesis of 1,4-dihydropyridines in an ionic liquid
Shaabani, Ahmad,Rezayan, Ali H.,Rahmati, Abbas,Sharifi, Masoumeh
, p. 77 - 81 (2006)
Hantzsch 1,4-dihydropyridine compounds were synthesized efficiently in high yields at room temperature within short times in 1,1,3,3-N,N,N′,N′- tetramethylguanidinium trifluoroacetate as ionic liquid using ultrasound irradiation. The ionic liquid can be recovered conveniently and reused efficiently. Springer-Verlag 2006.
g-C3N4@Ce-MOF Z-scheme heterojunction photocatalyzed cascade aerobic oxidative functionalization of styrene
Karimia, Meghdad,Sadeghia, Samira,Gavinehroudi, Reza Ghahremani,Mohebali, Haleh,Mahjoub, Alireza,Heydari, Akbar
, p. 6671 - 6681 (2021)
A special composite of the cerium-based metal-organic framework (Ce-UiO-66) modified with graphitic carbon nitride nanosheets (g-C3N4) has been synthesized. In order to make a comparison, a series of composites comprising g-C3N4and Ce-MOF were synthesized as well. Their structural features were investigated using Fourier transform infrared spectroscopy (FT-IR), powder X-ray diffraction (PXRD), sorption of nitrogen (BET and BJH), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), energy dispersive X-ray (EDX), transmission electron microscopy (TEM), X-ray fluorescence spectroscopy (XRF) and diffuse reflectance UV-Vis spectroscopy (UV-Vis DRS) and electron spin resonance (ESR) techniques. According to the obtained results, it was found that nanosheets of mesoporous g-C3N4act as linkers between the cerium sites, playing a critical role in the formation of composites. In fact, the embedded g-C3N4nanoparticles in the Ce-MOF cause a new kind of meso-porosity. Moreover, the coordination of nitrogen atoms in the graphitic carbon nitride structure to cerium atoms of the crystal brings about substantial changes in the optical properties, increasing the photoreactivity. On the other hand, since there is a physical contact between Ce-UiO-66 and g-C3N4in the composite, the unaltered pore volume and optical properties lead to the formation of a physical mixture rather than a composite. The g-C3N4@Ce-MOF as a photocatalyst was employed in photocatalytic aerobic oxidative Hantzsch pyridine synthesis of styrene and indicated high performance under visible light. The stability and reusability of g-C3N4@Ce-MOF were also examined and showed high efficiency up to the 5th run. Besides, the PXRD and FT-IR analyses taken from the retrieved g-C3N4@Ce-MOF nanocomposite confirmed the catalyst stability after the completion of the cascade aerobic oxidative reaction. Despite the photocatalytic performance, the synergistic effect of open metal sites in the MOF as Lewis acid and nitrogen in g-C3N4have greatly improved the efficiency of the catalyst. Moreover, the study of the reaction mechanism using ESR indicates the positive effect of composite formation on the performance of the photocatalytic aerobic oxidation reaction by the superoxide radical (O2˙—), as a selective oxidant species.
Alginic acid: A highly efficient renewable and heterogeneous biopolymeric catalyst for one-pot synthesis of the Hantzsch 1,4-dihydropyridines
Dekamin, Mohammad G.,Ilkhanizadeh, Siamand,Latifidoost, Zahra,Daemi, Hamed,Karimi, Zahra,Barikani, Mehdi
, p. 56658 - 56664 (2014)
Alginic acid, a naturally occurring polysaccharide, in its granular form and without any post-modification was found to be an efficient, environmentally benign, easily recoverable and low-cost catalyst for the clean and rapid synthesis of 1,4-dihydropiridine derivatives (DHPs) just based on its polysaccharide architecture. The Hantzsch pseudo-four-component reaction of ethyl or methyl acetoacetate, ammonium acetate and different aldehydes is catalyzed by alginic acid efficiently under mild conditions to afford the desired products in high to quantitative yields and clean reaction profiles. Avoiding the use of any transition metal, the use of a one-pot and multi-component procedure for the synthesis of DHPs, the reusability of the catalyst and operational simplicity are important features of this methodology.
Covalently anchored sulfonic acid on silica gel as an efficient and reusable heterogeneous catalyst for the one-pot synthesis of Hantzsch 1,4-dihydropyridines under solvent-free conditions
Gupta, Raman,Gupta, Rajive,Paul, Satya,Loupy, Andre
, p. 2835 - 2838 (2007)
A highly efficient one-pot synthesis of Hantzsch 1,4-dihydropyridines under solvent-free conditions catalyzed by sulfonic acid covalently anchored onto the surface of silica gel is reported here. All types of aldehydes, including aromatic, unsaturated, and heterocyclic aldehydes, gave excellent yields. The silica gel/sulfonic acid catalyst (SiO2-SO3H) is completely heterogeneous and can be recycled for eight consecutive runs without significant loss of activity. Georg Thieme Verlag Stuttgart.
