10354-30-0Relevant articles and documents
PPA-SiO 2 catalyzed one-pot synthesis of 1,4-dihydropyridines under solvent-free conditions
Khojastehnezhad, Amir,Moeinpour, Farid,Shams, Alireza
, p. 273 - 277 (2012)
Silica gel-supported polyphosphoric acid (PPA-SiO2) was found to be an efficient catalyst for the one-pot condensation reaction of aryl aldehydes, ethyl acetoacetate, and ammonium acetate to afford the corresponding 1,4-dihydropyridines in excellent yields. The main advantages of the present approach are short reaction times, clean reaction profiles, and simple experimental and work-up procedures.
Basicity and stability of urea deep eutectic mixtures
Simeonov,Afonso, Carlos A. M.
, p. 5485 - 5490 (2016)
The stability and basicity origin of some common urea based deep eutectic mixtures/solvents (DES) were studied. We have observed an unexpected Hantzsch dihydropyridine reaction in sorbitol/urea DES, where the source of ammonia was found not to be originated from the individual ingredients of the DES. Our results showed that decomposition of urea occurs in DES at lower than expected temperatures, namely below 100 °C and is enhanced in diol DES by the formation of carbonates causing their unexplained basicity. Carbohydrates and choline chloride (ChCl) DES exhibit lower rates of decomposition, while no decomposition was observed from neat urea or MeOH and EtOH urea solutions.
One-pot, three-component synthesis of 1,4-dihydropyridines in PEG-400
Wang, Xicun,Gong, Haipeng,Quan, Zhengjun,Li, Lei,Ye, Helin
, p. 3251 - 3258 (2011)
A series of Hantzsch 1,4-dihydropyridines were synthesized by one-pot condensation of aldehyde, β-dicarbonyl compound, and ammonium acetate in polyethylene glycol (PEG-400) at 90°C. This method has the advantages of good yields, less pollution, and simple reaction conditions. Copyright
A convenient ferric chloride catalyzed synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones under microwave irradiation
Tu, Shu-Jiang,Zhou, Jian-Feng,Cai, Pei-Jun,Wang, Hai,Feng, Jun-Cai
, p. 147 - 151 (2002)
A series of ethyl 4-aryl-6-methyl-1,2,3,4-tetrahydropyrimidin-2-one-5-carboxylates 4 were synthesized by the condensation of aromatic aldehydes, ethyl acetoacetate and urea in the presence of ferric chloride hexahydrate under microwave irradiation. The reactions were completed in 4-6 min with 87-92% yield.
An Efficient Synthesis of 4-Aryl-1,4-dihydropyridines Via VB1 Catalyzed Hantzsch Reaction
Fan, Chuangang,Song, Mingzhi
, p. 707 - 711 (2011)
An environmentally rapid and benign protocol for the synthesis of 4-aryl-1,4-dihydropyridines compounds using VB1 as a catalyst under microwave irradiation and solvent-free conditions has been achieved. The procedure is operationally simple, giving good to high product yield.
A new magnetically recoverable catalyst promoting the synthesis of 1,4-dihydropyridine and polyhydroquinoline derivatives via the Hantzsch condensation under solvent-free conditions
Taheri, Narges,Heidarizadeh, Fariba,Kiasat, Alireza
, p. 481 - 487 (2017)
In the current study, 1,4-dihydropyridine and polyhydroquinoline derivatives were efficiently synthesized under solvent-less conditions with a magnetic catalyst containing novel acidic ionic liquid functionalized silica modified Fe3O4 nanoparticles through a four component combination of β-ketoester, aldehydes and ammonium acetate (1, 2, 2). Several approaches have been reported for synthesizing these derivatives, while each of these approaches have some weaknesses including long time of reaction, excess of volatile organic solvent, low efficiency, costly reagents, complex operation, high temperatures, production of a number of side products, and difficult catalyst recovery. The simple operation, short time of reaction (5–30?min) and the high efficiency (80–94%) are the special advantages of this technique. The immobilized catalyst exhibited an appropriate thermal stability and excellent recyclability. Different methods such as FT-IR, SEM, EDX, TGA-DTA, and VSM were used to confirm and characterize the catalyst.
Hybrid pharmacophore-based drug design, synthesis, and antiproliferative activity of 1,4-dihydropyridines-linked alkylating anticancer agents
Singh, Rajesh K.,Prasad,Bhardwaj
, p. 1534 - 1545 (2015)
Two series of novel substituted 1,4-dihydropyridine derivatives incorporating nitrogen mustard pharmacophore hybrids without spacer DHP-M (4a-4d) and with ethyl spacer DHP-L-M (8a-8g) were designed and synthesized. They were subjected to in silico ADME prediction study to check their drug-like properties and evaluated for their cytotoxicity against: A 549 (lung), COLO 205 (colon), U 87 (glioblastoma), and IMR-32 (neuroblastoma) human cancer cell lines in vitro using 3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay against chlorambucil and docetaxel. Majority of the test compounds exhibited moderate to significant cytotoxic activity. The highest activity in all the investigated cancer cells was displayed by DHP-M (4a). This may be due to the less steric hindrance offered by 4a.
Urease: A highly biocompatible catalyst for switchable Biginelli reaction and synthesis of 1,4-dihydropyridines from the in situ formed ammonia
Tamaddon, Fatemeh,Ghazi, Somayeh
, p. 63 - 67 (2015)
Urease is a superior biocompatible catalyst for switching from the Biginelli reaction to urea-based synthesis of 1,4-dihydropyridines in water, where 100% switching occurs at 0.02 g/mL of enzyme. Hantzsch reaction with ammonium acetate (NH4OAc) is inefficiently catalyzed by urease (70%, 4 h), and heavy metal ions inhibit the urease-catalyzed reactions with urea or NH4OAc. Promotion of the urea-based Hantzsch reaction by urease and its inhibition with Hg2 + supports specificity of urease for in situ generation of ammonia, whereas the role of urease in further transformations is not so specific. The features of this enzymatic method are reusability, mild reaction conditions, biocompatibility, generality, and high yield of products.
One-pot synthesis of 1,4-dihydropyridine derivatives using the Fe2ZnAl2O7 catalyzed Hantzsch three-component reaction
Zargarzadeh, Reza,Akbari Dilmaghani, Karim,Nikoo, Abbas
, p. 1310 - 1316 (2021)
A facile, low-cost, and effective one-pot method was developed for the synthesis of 1,4-dihydropyridine derivatives with high yields through the three-component reaction of ammonium acetate, ethyl acetoacetate, and aromatic aldehydes using Fe2ZnAl2O7 as catalyst. The reaction was conducted at 70–80°C temperature under solvent free conditions. The developed method had some great advantages, including safe and clean reaction conditions, high to excellent product yields, short reaction time, and a novel and powerful heterogeneous catalyst. The developed heterogeneous solid catalyst had high efficiency and reusability in one-pot multi-component syntheses such that it was easily reused four to five times without significant loss in efficiency and product yield. The catalyst was characterized by scanning Electron Microscopy (SEM)/energy-dispersive X-ray spectroscopy (EDS) and X-ray diffraction techniques. N2 sorption isotherms of the prepared nanocomposite exhibited surface area 2.1313E+01 m2/g and total pore volume of 3.0957E-02 cm3/g. Substituted dihydropyridine derivatives were characterized and confirmed using 1H NMR and 13C NMR, and elemental spectral data.
Design, solvent free synthesis, and antimicrobial evaluation of 1,4 dihydropyridines
Murthy,Rajack, Abdul,Taraka Ramji,Jeson Babu,Praveen, Ch.,Aruna Lakshmi
, p. 6016 - 6023 (2012)
Here in, we report the usage of cellulose sulfuric acid as a heterogeneous eco friendly catalyst for the synthesis of 1,4 dihydropyridines under solvent free conditions via Hantzsch three component reaction of an aldehyde, ethyl acetoacetate and ammonium acetate at 100 °C for 2-5 h. In silico studies were performed on twenty two possible 1,4 dihydropyridines (DHPs) analogues against K+ channel receptor (KcsA). In order to validate in silico studies, thirteen compounds were synthesized and evaluated as antibacterials against twenty seven ESBL isolates of Klebsiella pneumoniae and Escherichia coli.
