- Ultrasound-Accelerated, Concise, and Highly Efficient Synthesis of 2-Oxazoline Derivatives Using Heterogenous Calcium Ferrite Nanoparticles and Their DFT Studies
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A rapid and operationally simple approach for synthesising biologically relevant 2-oxazoline derivatives has been developed through highly efficient ultrasound-promoted coupling reactions of thioamides and amino alcohols using calcium ferrite nanoparticles as heterogeneous catalysts. The major advantage of using ultrasound irradiation lies in the drastic reduction of reaction time as compared with conventional stirring. Furthermore, quantum chemical investigations for the synthesised 2-oxazoline derivatives have been carried out at the DFT/B3LYP/6-311 + G (d, p) level of theory to predict the optimized geometry. The molecular properties such as bond lengths, bond orders, Milliken charges, frontier molecular orbitals, global reactivity descriptors, molecular electrostatic potential map, and thermodynamic parameters of all the compounds have also been reported at the same level of theory.
- Atri, Shalu,Bendi, Anjaneyulu,Rao, G. B. Dharma,Raza, Mohd Jamshaiya,Sharma, Nutan
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- Nicorandil preparation method
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The invention discloses a nicorandil preparation method, which comprises the following steps: synthesis of 3-pyridyloxazolidine: under stirring, adding aminoethanol and a solid bromination reagent into an alcoholic solution of 3-pyridylaldehyde, stirring at room temperature until the 3-pyridylaldehyde is completely consumed, quenching the reaction system with a saturated sodium thiosulfate solution, extracting with ethyl acetate, and concentrating the organic phase to obtain a crude product 3-pyridyloxazolidine; and synthesis of nicorandil: dissolving the 3-pyridyloxazolidine in a solvent, adding nitrite, heating, introducing an oxygen-containing gas, stirring until the 3-pyridyloxazolidine is completely consumed, quenching with a saturated sodium sulfate solution, extracting with ethyl acetate, concentrating, adding the crude product into a 30% ethyl acetate n-hexane solution until dissloving, cooling to 10 DEG C, precipitating a solid, and filtering to obtain the nicorandil.
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Paragraph 0035-0040
(2020/04/06)
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- Cu(II) immobilized on Fe3O4@Agarose nanomagnetic catalyst functionalized with ethanolamine phosphate–salicylaldehyde schiff base: A magnetically reusable nanocatalyst for preparation of 2-substituted imidazolines, oxazolines, and thiazolines
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Herein we synthesized Cu(II) immobilized on Fe 3 O 4 @Agarose functionalized with ethanolamine phosphate–salicylaldehyde Schiff base (Fe 3 O 4 @Agarose/SAEPH 2 /Cu(II)) as a new and cost-effective nanomagnetic catalyst. The nanomagnetic catalyst was characterized by FT- IR, XRD, VSM, SEM- EDX, TEM, TGA, and ICP techniques and it was found that the particles were about 9–25 nm in size and spherical with entrapment of the Fe 3 O 4 particles in the hollow pore structure of the agarose. The prepared nanomagnetic catalyst showed excellent activity for preparation of 2-substituted imidazolines, oxazolines, and thiazolines. The catalyst is easy to prepare and exhibits higher catalytic activity than some commercially available copper sources. More importantly, this nanomagnetic catalyst can be easily recovered by using a permanent magnet and reused for at least seven cycles without significant deactivation.
- Zarei, Zeinab,Akhlaghinia, Batool
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p. 170 - 191
(2018/02/17)
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- Synthesis of heterocyclic 1,3-oxazolines from aldehydes with trimethylphenylammonium tribromide
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Various heterocyclic 1,3-oxazolines were prepared from aldehydes and aminoalcohols with trimethylphenylammonium tribromide at room temperature.
- Sayama, Shinsei
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p. 979 - 990
(2017/06/13)
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- A 2 - substituted oxazoline or 2 - substituted piperazine synthetic method (by machine translation)
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The invention discloses a method for synthesizing 2 - substituted oxazoline or 2 - substituted oxazine new method, by nitrile and amino ethanol or 3 - amino - 1 - propanol as raw material, in the absence of solvent, can be used for the recycling of the sulfur to induce synthesis of 2 - substituted oxazoline and 2 - substituted piperazine. The method of the invention has low cost, simple reaction process, mild reaction conditions, the reaction time is short, the yield and the like, is suitable for the industrial generation. (by machine translation)
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Paragraph 0018; 0020; 0021; 0032;
(2017/08/25)
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- Highly efficient synthesis of β-nitrate ester carboxamides through the ring-opening of 2-oxazolines
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A novel method for the synthesis of β-nitrate ester carboxamides using non-corrosive tert-butyl nitrite (TBN) as the nitro source and easily available oxygen as the oxidant has been developed. Variously substituted 2-oxazolines were efficiently ring-opened to deliver the corresponding products in excellent yields. Notably, this reaction provides fast access to pharmaceuticals such as nicorandil.
- Qiao, Kai,Yuan, Xin,Wan, Li,Zheng, Ming-Wei,Zhang, Dong,Fan, Bing-Bing,Di, Zhe-Chen,Fang, Zheng,Guo, Kai
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supporting information
p. 5789 - 5793
(2017/12/26)
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- Synthesis of Functionalized Pyridines via a Regioselective Oxazoline Promoted C-H Amidation Reaction
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The first Rh-catalyzed C-H amidation of pyridines is reported. The incorporation of a substituent at the C2 position both is crucial to the success of this transformation and provides considerable scope for further elaboration of the resulting products. Among these compounds, 2-chloropyridines allow access to a selection of intermediates including a versatile azaquinazoline scaffold.
- Maiden, Tracy M. M.,Swanson, Stephen,Procopiou, Panayiotis A.,Harrity, Joseph P. A.
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p. 3434 - 3437
(2016/07/26)
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- Willgerodt–Kindler reaction-driven one pot solventless entry to 2-oxazolines
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We report an efficient and green protocol for the synthesis of 2-oxazolines by the reaction of aromatic nitriles with β-aminoalcohols using sulfur under solvent-free conditions. The reaction occurs via the Willgerodt-Kindler mechanism followed by transami
- Bansal, Shivani,Gupta, Poonam,Halve
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p. 971 - 974
(2016/07/06)
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- Copper N-Heterocyclic Carbene Complexes As Active Catalysts for the Synthesis of 2-Substituted Oxazolines from Nitriles and Aminoalcohols
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The reaction between nitriles and aminoalcohols to access 2-substituted oxazolines was investigated. Using copper-NHC complexes, various nitriles were successfully converted into the corresponding oxazolines, under milder and less wasteful conditions than those of previously reported methods.
- Trose, Michael,Lazreg, Fa?ma,Lesieur, Mathieu,Cazin, Catherine S. J.
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p. 9910 - 9914
(2015/11/03)
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- Synthesis of 2-aryl/heteroaryloxazolines from nitriles under metaland catalyst-free conditions and evaluation of their antioxidant activities
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The synthesis of structurally diverse 2-aryl/heteroaryloxazolines from nitriles and aminoalcohols has been achieved under metal- and catalyst-free conditions in good to excellent yields. An array of functional groups are well-tolerated, thus, allowing the introduction of many important biologically active motifs such as azoles, ring-fused azoles, saturated heterocyclics, and amines in 2-aryloxazoline scaffolds. An evaluation of the antioxidant properties using the DPPH (diphenyl picryl hydrazyl) assay method shows the pyrrole-functionalized 2-aryloxazoline to be the best antioxidant among all the synthesized 2-aryl/heteroaryloxazolines.
- Garg, Parul,Chaudhary, Shweta,Milton, Marilyn D.
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p. 8668 - 8677
(2015/01/08)
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- S-Co(II) cascade catalysis: Cyclocondensation of aromatic nitriles with alkamine
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A solvent-free S/Co(NO3)2 cascade catalyzed cyclocondensation reaction of aromatic nitriles with 3-amino-1-propanol or 2-aminoethanol has been successfully developed under thermal and microwave conditions. By this two-component protocol, mono- and bis-oxazines and oxazolines were selectively synthesized both in good to excellent yields and short reaction times. This catalytic system exhibits excellent chemoselectivity, and can be reused at least seven times without significant loss of activity in subsequent reactions.
- Ge, Haixia,Liu, Ping,Li, Xiangnan,Sun, Wei,Li, Jianli,Yang, Bingqin,Shi, Zhen
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p. 6591 - 6597
(2013/07/26)
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- Polynuclear copper(ii) pyrazolate complexes: Temperature-dependent protonolysis reactions, crystal structures and high catalytic activity toward the condensation of nitriles with 2-aminoalcohol
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Reaction of Cu(OAc)2·H2O and 1H-pyrazole-3,5-dicarboxylic acid dimethyl ester (Hdcmpz) in MeOH at room temperature afforded one tetranuclear Cu(ii)/pyrazolate complex [{Cu 2(μ-OAc)2}2(μ-dcmpz)2/
- Wang, Ling,Guo, Bin,Li, Hong-Xi,Li, Qi,Li, Hai-Yan,Lang, Jian-Ping
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p. 15570 - 15580
(2013/11/06)
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- A mild and efficient synthesis of 2-oxazolines via transamidation- cyclodehydrosulfurisation of thioamides with 2-aminoethanol
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Transamidation of thioamides with 2-aminoethanol, followed by cyclodehydrosulfurisation of the resultant N-(β-hydroxyethyl)thioamides, has been utilised for the mild and efficient synthesis of 2-oxazolines. The developed protocol was found to be of general applicability. Georg Thieme Verlag KG Stuttgart · New York.
- Goud, D. Raghavender,Pathak, Uma
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p. 3678 - 3682
(2013/02/22)
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- A general and efficient palladium-catalyzed carbonylative synthesis of 2-aryloxazolines and 2-aryloxazines from aryl bromides
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Oxazoline is OK! A general and efficient method for the synthesis of oxazolines has been developed (see scheme). This allowed the preparation of 27 five-membered-ring heterocycles and 11 six-membered-ring heterocycles in moderate to good yields. Copyright
- Wu, Xiao-Feng,Neumann, Helfried,Neumann, Stephan,Beller, Matthias
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p. 13619 - 13623
(2013/01/15)
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- Trichloroisocyanuric acid as an efficient homogeneous catalyst for the chemoselective synthesis of 2-substituted oxazolines, imidazolines and thiazolines under solvent-free condition
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Trichloroisocyanuric acid, as a commercially available and inexpensive catalyst, was used in a new, facile and efficient procedure for the synthesis of 2-oxazolines, 2-imidazolines and 2-thiazolines through the reaction of nitriles with 2-aminoethanol, ethylenediamine or 2-aminoethanethiol under solvent-free conditions.
- Hojati, Seyedeh Fatemeh,Nezhadhoseiny, Seyede Atefe
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p. 1181 - 1189,9
(2020/09/14)
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- A powerful palladium-catalyzed multicomponent process for the preparation of oxazolines and benzoxazoles
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Efficient and convenient three-component couplings of an aryl halide, isocyanide, and an amino alcohol under palladium catalysis provide a range of oxazolines and benzoxazoles in excellent yield.
- Boissarie, Patrick J.,Hamilton, Zoe E.,Lang, Stuart,Murphy, John A.,Suckling, Colin J.
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supporting information; experimental part
p. 6256 - 6259
(2012/01/06)
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- Synthesis of 2-oxazolines via boron esters of N-(2-hydroxyethyl) amides
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A new, convenient, one-pot process is presented for the synthesis of 2-oxazolines in high yields (75-94%) via boron esters of N-(2-hydroxyethyl) amides. The procedure involves thermolysis of the boron esters at 240-260 °C, in the presence of solid CaO as an acid scavenger and allows the preparation of oxazolines from hydroxyethyl amides of aliphatic and aromatic monocarboxylic acids.
- Ilkgul, Baris,Gunes, Deniz,Sirkecioglu, Okan,Bicak, Niyazi
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experimental part
p. 5313 - 5315
(2010/11/03)
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- Preparation of an improved sulfonated carbon-based solid acid as a novel, efficient, and reusable catalyst for chemoselective synthesis of 2-oxazolines and bis-oxazolines
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A highly sulfonated carbon as an efficient, recyclable, nontoxic, and green solid acid catalyst was readily synthesized by simultaneous sulfonation, dehydration, and carbonization of sucrose in sulfuric acid and was characterized by FT-IR, TG-DTG, XRD, and CHNS analysis, neutralization potentiometric titration, and SEM techniques. This new catalyst was used for preparation of 2-oxazolines and bis-oxazolines by reaction of β-aminoethanol with nitriles under reflux conditions. Sonication of this system enhanced the catalytic activity of the carbon-based solid acid and led to higher product yields and shorter reaction times. Another advantage of the system under ultrasonic irradiation is the ability to carry out large-scale reactions. In two cases, the catalyst was reused several times without loss of its activity.
- Mirkhani, Valiollah,Moghadam, Majid,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Mahdavi, Mohammad
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experimental part
p. 1489 - 1494
(2010/07/04)
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- A novel and chemoselective synthesis of 2-aryloxazolines and bis-oxazolines catalyzed by Bi(III) salts
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Different arylnitriles react with β-aminoalcohols in the presence of catalytic amounts of Bi(III) salts such as Bi(TFA)3, Bi(OTf) 3 and BiOClO4·XH2O producing the corresponding 2-aryl-oxazolines in high yields. Selective synthesis of mono- and bis-oxazolines from dicyanobenzenes and selective conversion of arylnitriles to their 2-oxazolines in the presence of alkylnitriles can be considered as noteworthy advantages of this method. Georg Thieme Verlag Stuttgart.
- Mohammadpoor-Baltork, Iraj,Khosropour, Ahmad Reza,Hojati, Seyedeh Fatemeh
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p. 2747 - 2750
(2007/10/03)
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