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103183-96-6

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103183-96-6 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 103183-96-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,3,1,8 and 3 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 103183-96:
(8*1)+(7*0)+(6*3)+(5*1)+(4*8)+(3*3)+(2*9)+(1*6)=96
96 % 10 = 6
So 103183-96-6 is a valid CAS Registry Number.

103183-96-6Relevant articles and documents

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.

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.

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

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.

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.

Synergistic catalytic effect between ultrasound waves and pyrimidine-2,4-diamine-functionalized magnetic nanoparticles: Applied for synthesis of 1,4-dihydropyridine pharmaceutical derivatives

Taheri-Ledari, Reza,Rahimi, Jamal,Maleki, Ali

, (2019)

A convenient strategy for synthesis of the various derivatives of 1,4-dihydropyridine (1,4-DHP), as one of the most important pharmaceutical compounds, is presented in this study. For this purpose, firstly, magnetic iron oxide nanoparticles (Fe3O4 NPs) were fabricated and suitably coated by silica network (SiO2) and trimethoxy vinylsilane (TMVS). Then, their surfaces were well functionalized with pyrimidine-2,4-diamine (PDA) as the main active sites for catalyzing the synthesis reactions. In this regard, the performance of three different methods including reflux, microwave (MW) and ultrasound wave (USW) irradiations have been comparatively monitored via studying various analyses on the fabricated nanocatalyst (Fe3O4/SiO2-PDA). Concisely, high efficiency of the USW irradiation (in an ultrasound cleaning bath with a frequency of 50 kHz and power of 250 W/L) has been well proven through the investigation of the main factors such as excellent surface-functionalization, core/shell structure conservation, particle uniformity, close size distribution of the particles, and great inhibition of the particle aggregation. Then, the effectiveness of the USW irradiation as a promising co-catalyst agent has been clearly demonstrated in the 1,4-DHP synthesis reactions. It has been concluded that the USW could provide more appropriate conditions for activation of the catalytic sites of Fe3O4/SiO2-PDA NPs. However, high reaction yields (89%) have been obtained in the short reaction times (10 min) due to the substantial synergistic effect between the presented nanocatalyst and USW.

An efficient and recyclable 3D printed α-Al2O3 catalyst for the multicomponent assembly of bioactive heterocycles

Azuaje, Jhonny,Tubío, Carmen R.,Escalante, Luz,Gómez, Mónica,Guitián, Francisco,Coelho, Alberto,Caama?o, Olga,Gil, Alvaro,Sotelo, Eddy

, p. 203 - 210 (2017)

A catalytic methodology is reported that enables the efficient, operationally simple and environmentally friendly synthesis of diverse 1,4-dihydropyridines and 3,4-dihydropyrimidin-2(1H)-ones, including some relevant drugs and pharmacologically active derivatives. This strategy is based on the use of a 3D printed Al2O3 woodpile material that was sintered to generate a rigid structure with controlled porosity and noteworthy catalytic performance. The 3D printed Al2O3 catalyst exhibits remarkable efficacy as a Lewis acid in Biginelli and Hantzsch reactions and it can be recovered and reused ten times without any decrease in the activity. Remarkable E factors, excellent recyclability and scalability, broad substrate scope, short reaction times, excellent yields, solvent-free conditions and easy isolation procedures are key features of this methodology.

Scaling up of dihydropyridine ester synthesis by using aqueous hydrotrope solutions in a continuous microwave reactor

Khadilkar, Bhushan M.,Madyar, Virendra R.

, p. 452 - 455 (2001)

We report here the scaling up of clinically important dihydropyridine by using a continuous microwave reactor (CMR). We also report the use of aqueous hydrotrope solution as a cheap, safe and "green" alternative to organic solvent to carry out homogeneous reactions under microwave heating. We have studied different aqueous hydrotrope solutions for the reaction in batch as well as continuous-flow process.

Hantzsch Reaction Starting Directly from Alcohols through a Tandem Oxidation Process

Liu, Xiaobing,Liu, Bin

, (2017)

A Br?nsted acidic ionic liquid, 3-(N,N-dimethyldodecylammonium) propanesulfonic acid hydrogen sulphate ([DDPA][HSO4]), has been successfully applied to catalyze sequential oxidation of aromatic alcohols with NaNO3 followed by their c

Synthesis and antioxidant activity of a series of novel 3-chalcone-substituted 1,4-dihydropyridine derivatives

Sun, Hao,Shang, Chengxiang,Jin, Longfei,Zhang, Jian

, p. 239 - 243 (2012)

New 3-chalcone-substituted 1,4-dihydropyridine (DHP) derivatives have been synthesized based on dimethyl or diethyl 2,6-dimethyl-4-phenyl-1,4-DHP-3,5- dicarboxylate. Their structures were confirmed by IR, 1H NMR, 13C NMR, and elemental analyses. The synthesized compounds were also screened for antioxidant properties.

Novel Magnetically Separable Sulfated Boric Acid Functionalized Nanoparticles for Hantzsch Ester Synthesis

Azizi, Kobra,Azarnia, Jamshid,Karimi, Meghdad,Yazdani, Elahe,Heydari, Akbar

, p. 1810 - 1813 (2016)

A novel, separable, solid-acid catalyst consisting of sulfated boric acid nanoparticles immobilized on a silica-coated magnetite support was prepared. This catalyst permits the preparation of dihydropyridine derivatives (Hantzsch esters) by condensation of an aldehyde with two equivalents of a β-keto ester in the presence of ammonium acetate. The catalyst can be recovered and recycled.

Aqueous hydrotrope solution as a safer medium for microwave enhanced Hantzsch dihydropyridine ester synthesis

Khadilkar, Bhushan M.,Gaikar, Vilas G.,Chitnavis, Ashish A.

, p. 8083 - 8086 (1995)

Hantzsch esters are prepared for the first time, by condensing alkyl β-aminocrotonate, aldehyde and alkyl acetoacetate in aqueous sodium butylmonoglycosulphate (NaBMGS) as a safe reaction medium in an unmodified domestic microwave oven.

Synthesis of Hantzsch 1,4-dihydropyridines under solvent-free condition using Zn[(L)proline]2 as Lewis acid catalyst

Sivamurugan,Kumar, R. Suresh,Palanichamy,Murugesan

, p. 969 - 974 (2005)

The present short communication describes a Lewis acid (Zn[(L)proline] 2) catalysed one pot synthesis of Hantzsch 1,4-dihydropyridine (DHP) derivatives under solvent-free condition by conventional heating and microwave irradiation. The Lewis acid catalyst Zn[(L)proline]2 used in this reaction afford moderate to good yield. The catalyst is reusable upto five cycles without appreciable loss of its catalytic activity.

Synthesis of pyridinium salts from N-substituted dihydropyridines with BF3OEt2 in the absence of added oxidants

Guanaes, Lais D.,Ducatti, Diogo R.B.,Duarte, M. Eugênia R.,Barreira, Sandra M.W.,Noseda, Miguel D.,Gon?alves, Alan G.

, p. 2001 - 2004 (2015)

Abstract N-Substituted dihydropyridines were converted into pyridinium salts with BF3OEt2 as aromatization promoter in reactions that could be conducted without the need of the usually added oxidizing agents, such as quinones, nitrat

Synthesis of 1,4-dihydropyridines using Ce(SO4)2-SiO2 as catalyst under solvent-free conditions

Pei, Wen,Wang, Qin,Li, Xiaonian,Sun, Li

, p. 483 - 486 (2010)

A facile and efficient one-pot synthesis of 1,4-dihydropyridines from aldehyde, 1,3-dicarbonyl compounds and ammonium acetate in the presence of Ce(SO4)2-SiO2 at 80 °C under solvent-free conditions is described. Compared with the classical Hantzsch reaction, this novel method consistently has the advantages of excellent yields and short reaction time.

A simple and efficient one-pot synthesis of Hantzsch 1,4-dihydropyridines using silica sulphuric acid as a heterogeneous and reusable catalyst under solvent-free conditions

Kolvari, Eskandar,Zolfigol, Mohammad Ali,Koukabi, Nadiya,Shirmardi-Shaghasemi, Behzad

, p. 898 - 902 (2011)

A simple, inexpensive and efficient one-pot synthesis of 1,4-dihydropyridine derivatives under solvent-free conditions using silica sulphuric acid (SSA) as a heterogeneous and recyclable catalyst is reported.

Ultrasound-mediated, uranyl nitrate hexahydrate-catalyzed synthesis of 1,4-dihydropyridines under mild conditions

Palakshi Reddy,Sarveswari,Vijayakumar

, p. 6877 - 6883 (2015)

Abstract Synthesis of 1,4-dihydropyridines by three-component condensation reaction of aldehyde, 1,3-dicarbonyl compounds, and ammonium acetate have been found to be efficiently catalyzed by uranyl nitrate hexahydrate [UO2(NO3)2 ·6H2O] at room temperature under ultrasound irradiation. This novel synthetic method offers the advantages of high yields, short reaction times, simplicity, and easy workup compared to the conventional methods reported in the literature.

1-Methylimidazolium trifluoroacetate [Hmim]Tfa: Mild and efficient Bronsted acidic ionic liquid for Hantzsch reaction under microwave irradiation

Avalani, Jemin R.,Patel, Devji S.,Raval, Dipak K.

, p. 1091 - 1096 (2012)

One pot synthesis of 1,4-dihydropyridine derivatives was achieved via condensation of various β-ketoesters with aromatic/aliphatic aldehydes and ammonium acetate. The reaction was catalysed by a stable and reusable Bronsted acidic ionic liquid (IL), 1-methyl-imidazolium trifluoroacetate ([Hmim]Tfa), under microwave (MW) irradiation. The synergistic combination ofMWwith IL can potentially go a long way tomeet the increasing demand for chemical processes. This homogeneous catalytic procedure is simple and efficient. The catalyst can be reused at least four times with almost complete retention in its activity. Indian Academy of Sciences.

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Van Bergen et al.

, p. 2377,2383 (1978)

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Vanadium(IV and v) complexes of pyrazolone based ligands: Synthesis, structural characterization and catalytic applications

Maurya, Mannar R.,Sarkar, Bithika,Avecilla, Fernando,Correia, Isabel

, p. 17343 - 17364 (2016)

The ONO donor ligands obtained from the condensation of 4-benzoyl-3-methyl-1-phenyl-2-pyrazoline-5-one (Hbp) with benzoylhydrazide (H2bp-bhz I), furoylhydrazide (H2bp-fah II), nicotinoylhydrazide (H2bp-nah III) and isonicotinoylhydrazide (H2bp-inh IV), upon treatment with [VIVO(acac)2], lead to the formation of [VIVO(bp-bhz)(H2O)] 1, [VIVO(bp-fah)(H2O)] 2, [VIVO(bp-nah)(H2O)] 3 and [VIVO(bp-inh)(H2O)] 4, respectively. At neutral pH the in situ generated aqueous K[H2VVO4] reacts with ligands I and II, forming potassium salts, K(H2O)2[VVO2(bp-bhz)] 5 and K(H2O)2[VVO2(bp-fah)] 6, while ligands III and IV give neutral complexes, [VVO2(Hbp-nah)] 9 and [VVO2(Hbp-inh)] 10, respectively. Acidification of aqueous solutions of 5 and 6 with HCl also gives neutral complexes [VVO2(Hbp-bhz)] 7 and [VVO2(Hbp-fah)] 8, respectively. Complexes 1-4, upon slow aerial oxidation in methanol, convert into monooxidovanadium(v) complexes, [VVO(bp-bhz)(OMe)] 11, [VVO(bp-fah)(OMe)] 12, [VVO(bp-nah)(OMe)] 13 and [VVO(bp-inh)(OMe)] 14, respectively. All complexes were characterized by various spectroscopic techniques like FT-IR, UV-visible, EPR (for complexes 1-4) and NMR (1H, 13C and 51V), elemental analysis, thermogravimetry and single crystal X-ray diffraction (for complexes 5-10 and 12). In the solid state, all complexes characterized by X-ray diffraction show the metal ion 5-coordinated in a distorted square pyramidal geometry. Complexes 11-14 were tested as catalysts for the one-pot three-component (ethylacetoacetate, benzaldehyde and ammonium acetate) dynamic covalent assembly, via Hantzsch reaction, using hydrogen peroxide as oxidant in solution and under solvent-free conditions. The complexes are also active catalysts for the oxidation of tetralin to tetralone with H2O2 as oxidant. The influence of the amounts of catalyst and oxidant, and solvent, temperature and time on the catalyzed reactions was investigated.

Synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 1,4-dihydropyridines using ammonium carbonate in water

Tamaddon, Fatemeh,Razmi, Zahra,Jafari, Abbas Ali

, p. 1187 - 1189 (2010)

Various known and new 3,4-dihydropyrimidin-2(1H)-ones and 1,4-dihydropyridines are prepared efficiently via Biginelli and Hantzsch reactions using ammonium carbonate in water. Competition between Biginelli and Hantzsch reactions is observed with pyridine carbaldehydes. Using this methodology, Hantzsch esters are synthesized in higher yields and purities than with other procedures without the use of a catalyst or an organic solvent.

Ferric Sulfasalazine Sulfa Drug Complex Supported on Cobalt Ferrite Cellulose; Evaluation of Its Activity in MCRs

Rostamizadeh, Shahnaz,Daneshfar, Zahra,Khazaei, Ali

, p. 2091 - 2114 (2020/01/31)

Abstract: The green and nano catalyst was simply prepared through the reaction of ferric sulfasalazine with nanomaterial CoFe2O4-cellulose as a magnetic biopolymer surface. This novel heterogeneous organometallic catalyst was charact

Metal free biomimetic deaminative direct C-C coupling of unprotected primary amines with active methylene compounds

Ghosh, Santanu,Jana, Chandan K.

supporting information, p. 10153 - 10157 (2019/12/26)

An unprecedented direct C-C coupling reaction of unprotected primary amines with active methylene compounds is reported. The reaction involves a biomimetic deamination of amines which was achieved under conditions free of metallic reagents and strong oxidizing agents. A wide range of primary amines was reacted with different active methylene compounds to provide structurally diverse trisubstituted alkenes and dihydropyridines. A kinetic study revealed an activation barrier of 10.1 kcal mol-1 for the conversion of a key intermediate of the reaction.

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