- N-bromosuccinimide (NBS)-promoted, three-component synthesis of α,β-unsaturated isoxazol-5(4H)-ones, and spectroscopic investigation and computational study of 3-methyl-4-(thiophen-2-ylmethylene)isoxazol-5(4H)-one
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A three-component, NBS-promoted synthesis of α,β-unsaturated isoxazol-5(4H)-ones by reaction of aromatic aryl or hetero-aryl aldehydes, hydroxylamine hydrochloride, and 1,3-dicarbonyl compounds (ethyl acetoacetate or ethyl 4-chloroacetoacetate), under mild reaction conditions at room temperature is described. This simple, efficient, and clean reaction is an expeditious means of obtaining the corresponding isoxazol-5(4H)-one derivatives in good to high yields. Geometrical properties and vibrational wavenumbers of 3-methyl-4-(thiophen-2-ylmethylene)isoxazol-5(4H)-one (MTISO) were predicted by use of density functional theory (DFT) by use of the B3LYP level with the 6-311++G(d,p) and 6-311++G(2d,p) basis sets. Results indicate that the B3LYP method enables satisfactory prediction of vibrational frequencies and structural data. The absorption spectra of MTISO in solvents of different polarity were studied at room temperature. The UV-visible spectrum of the compound was recorded and such electronic properties as the energies of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) were determined by the time-dependent DFT (TD-DFT) approach. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization was studied by NBO analysis. A molecular electrostatic potential map (MEP) of the compound was also studied to predict reactive sites. Reactivity descriptors, Fukui functions, and electrophilic sites were found and are discussed. The thermal stability of MTISO was studied by thermogravimetric analysis (TGA).
- Kiyani, Hamzeh,Kanaani, Ayub,Ajloo, Davood,Ghorbani, Fatemeh,Vakili, Mohammad
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- Fruit Extract of Averrhoa bilimbi: A Green Neoteric Micellar Medium for Isoxazole and Biginelli-Like Synthesis
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A transition metal/ligand/additive/promoter-free synthesis of 3-methyl-4-arylmethylene-isoxazol-5(4H)-ones and the Biginelli-like synthesis is carried out in a natural acidic medium of Averrhoa bilimbi extract (ABE) with cleaner and facile approach smenti
- Patil, Bhagyashree M.,Shinde, Sachinkumar K.,Jagdale, Ashutosh A.,Jadhav, Swati D.,Patil, Suresh S.
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p. 4369 - 4398
(2021/09/11)
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- An efficient solvent-free synthesis of 3,4-disubstituted isoxazole-5(4H)-ones using microwave irradiation
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I have reported one-pot and three-component synthesis of 3-mehyl-4-arylmethyleneisoxazol-5(4H)-ones using microwave radiation under the solvent-free conditions, in the presence of potassium bromide as the catalyst. The method has given the products in hig
- Kulkarni, Pramod
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- Synthetic enzyme-catalyzed multicomponent reaction for Isoxazol-5(4H)-one Syntheses, their properties and biological application; why should one study mechanisms?
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In this work, we describe the application of a synthetic enzyme (synzyme) as the catalyst to promote the multicomponent synthesis of isoxazol-5(4H)-one derivatives. The catalytic system could be used up to 15 times without any notable loss of its activity
- Oliveira, Gabriela H. C.,Ramos, Luciana M.,de Paiva, Raíssa K. C.,Passos, Saulo T. A.,Sim?es, Marina M.,Machado, Fabricio,Correa, José R.,Neto, Brenno A. D.
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p. 1514 - 1531
(2021/03/01)
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- Cu/TCH-pr&at;SBA-15 nano-composite: A new organometallic catalyst for facile three-component synthesis of 4-arylidene-isoxazolidinones
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A copper complex supported on SBA-15 nanoparticles (Cu/TCH-pr&at;SBA-15) was synthesized by the post-synthesis modification of nano-mesoporous silica with 3-chloropropyltriethoxysilane (CPTES) and thiocarbohydrazide (TCH) and subsequent metal-ligand coord
- Dadras, Akbar,Kalhor, Mehdi,Sajjadi, Seyed Mehdi
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p. 27439 - 27446
(2020/08/17)
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- One-pot three-component synthesis of isoxazole using ZSM-5 as a heterogeneous catalyst
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A mild and convenient route for the synthesis of isoxazole derivatives has been developed using ZSM-5 as a heterogeneous catalyst. The reaction was carried out under a solvent-free condition to afford the desired products in good yields. A variety of func
- Hatvate, Navnath T.,Ghodse, Shrikant M.
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p. 3676 - 3683
(2020/09/09)
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- Green synthesis of 3,4-disubstituted isoxazol-5(4H)-ones using ZnO@Fe3O4 core–shell nanocatalyst in water
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An effective and environmentally benign methodology for the synthesis of isoxazol-5(4H)-one derivatives has been developed using a ZnO@Fe3O4 core–shell nanocatalytic system. The one-pot, multicomponent reaction of an aromatic/heteroc
- Shanshak,Budagumpi, Srinivasa,Ma?ecki, Jan Grzegorz,Keri, Rangappa S.
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- Facile and expedient synthesis of α,β-unsaturated isoxazol-5(4H)-ones under mild conditions
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Abstract: It was found that nano-SiO2–H2SO4 was catalyzed by the three-component cyclocondensation of aryl/heteroaryl aldehydes, hydroxylamine hydrochloride, and β-ketoesters toward the synthesis of α,β-unsaturated?isoxazol-5(4H)-ones under green conditions. The reaction yielded the corresponding heterocycles at room temperature in relatively shorter reaction times. It merits mentioning that the mild conditions allow the synthesis of several α,β-unsaturated?isoxazol-5(4H)-ones using this method. In this study, some new derivatives of isoxazolones were also synthesized and characterized. It is efficient, clean, simple, safe, and ecologically friendly. This straightforward method is cost-effective and requires no preparation of reactants. The three-component annulation was performed without using energy sources, for example, heat, ultrasound wave, and microwave irradiation. Graphic abstract: [Figure not available: see fulltext.].
- Ghorbani, Fatemeh,Kiyani, Hamzeh,Pourmousavi, Seied Ali
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p. 943 - 959
(2019/11/13)
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- Preparation and characterization of supported bimetallic gold–iron nanoparticles, and its potential for heterogeneous catalysis
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Bimetallic gold–iron catalysts supported on ZrO2 and TiO2 were prepared by under potential deposition. The characterization of the catalysts was performed using an inductively coupled plasma, energy-dispersive spectroscopy, diffuse r
- Ferouani, Ghaniya,Ameur, Nawal,Bachir, Redouane
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p. 1373 - 1387
(2019/11/16)
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- Synthesis and characterization of nanocrystalline hydroxyapatite and its catalytic behavior towards synthesis of 3,4-disubstituted isoxazole-5(4H)-ones in water
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In the present work, the nanocrystalline particles of hydroxyapatite (HAp) using an easy alkoxide-based sol–gel technique including triethyl phosphate [PO (OC2H5)3] and Ca (NO3)2·4H2O as P and Ca precursors have been synthesized. The sample characterization was performed by X-ray diffraction, Fourier transform-infrared analysis, scanning electron microscopy, thermal analysis (thermogravimetric analysis/differential thermal analysis), and elemental analysis of energy-dispersive X-ray analysis. It is interesting that single phase of HAp was obtained at a low firing temperature of 500°C. Modified Scherrer equation as the Williamson?Hall method was applied for the measurement of crystallite size distributions and micro-strain of the sample. The determined crystallite size by complementary technique of transmission electron microscopy has good consistency with those obtained from the Scherrer formula. Moreover, we reported the one-pot synthesis of 3,4-disubstituted isoxazole-5(4H)-ones through the aqueous solution reaction of three components of ethyl acetoacetate, hydroxylamine hydrochloride and various aromatic aldehydes at room temperature. This protocol offers several advantages, including a simple work-up procedure, very short reaction times (under 25?min), in accordance with the principles of green chemistry, recyclability, excellent yields (87–98%) and environmentally friendly.
- Maleki, Behrooz,Chahkandi, Mohammad,Tayebee, Reza,Kahrobaei, Sepideh,Alinezhad, Heshmatollah,Hemmati, Saba
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- An expeditious synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4H)-ones using aqueous extract of acacia concinna pods as a natural surfactant catalyst
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An aqueous extract of Acacia concinna pods has been employed as a competent and effective natural surfactant type catalyst for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4H)-one analogs through one-pot, three-component reaction of β-ketoester,
- Kadu, Vinod R.,Gholap, Somnath S.
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p. 319 - 326
(2020/01/03)
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- A novel dicationic ionic liquid as a highly effectual and dual-functional catalyst for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4H)-ones
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Abstract: A novel dicationic ionic liquid, N,N,N′,N′-tetramethyl-N,N′-bis(sulfo)ethane-1,2-diaminium mesylate [TMBSED][OMs]2), has been produced, and identified by analysis of its 1H NMR, 13C NMR, FT-IR, mass and thermal g
- Irannejad-Gheshlaghchaei, Navid,Zare, Abdolkarim,Sajadikhah, Seyed Sajad,Banaei, Alireza
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p. 6253 - 6266
(2018/06/04)
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- A green and efficient synthesis of isoxazol-5(4H)-one derivatives in water and a DFT study
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A series of 4-arylmethylene-3-methylisoxazol-5(4H)-one derivatives are obtained via treating ethyl acetoacetate, hydroxylamine hydrochloride and variety of aromatic aldehyde compounds in the presence of antimony trichloride as an efficient catalyst in aqu
- Pourmousavi, Seied Ali,Fattahi, Hamid Reza,Ghorbani, Fatemeh,Kanaani, Ayoub,Ajloo, Davood
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p. 455 - 469
(2018/03/29)
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- Facile Heterocyclic Synthesis and Antibacterial Activity of Substituted Isoxazol-5(4H)-ones
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An efficient, simple, and green procedure for the synthesis of isoxazol-5(4H)-one derivatives are described here through a convenient one-pot, three-component reaction at room temperature. The title compounds are isolated in high to excellent yields and a
- Ferouani, Ghaniya,Nacer, Amina,Ameur, Nawal,Bachir, Redouane,Ziani-Cherif, Chewki
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p. 459 - 464
(2018/04/23)
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- Sulfated polyborate catalyzed expeditious and efficient three-component synthesis of 3-methyl-4-(hetero)arylmethylene isoxazole-5(4H)-ones
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A rapid and highly efficient methodology for the synthesis of 3-methyl-4-(hetero)arylmethylene isoxazole-5(4H)-ones has been developed using sulfated polyborate as a catalyst. The multicomponent reaction of an aromatic/heterocyclic aldehyde, hydroxylamine
- Patil, Manisha S.,Mudaliar, Chirag,Chaturbhuj, Ganesh U.
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supporting information
p. 3256 - 3261
(2017/07/27)
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- Expeditious green synthesis of 3,4-disubstituted isoxazole-5(4H)-ones catalyzed by nano-MgO
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In this work, it was found that magnesium oxide nanoparticles (nano-MgO) catalyzed one-pot three-component reaction of hydroxylamine hydrochloride with aryl aldehydes (or heteroaryl aldehydes) and β-oxoesters to synthesize some biologically active isoxazole-5(4H)-one-based heterocycles. The reactions were completed using 3?mol% catalyst loading in aqueous medium at room temperature. Nano-MgO was synthesized by precipitation and hydrothermal treatment of aqueous salt solution. The structure of the nano-MgO was characterized by X-ray diffraction (XRD) and scanning electron microscopy (SEM) analyses. The presented environmentally friendly heterocyclization offers some interesting merits, including safety, high product yield, mild conditions, low cost, minimal waste, good atom efficiency, catalyst recoverable, energy efficiency, avoidance of hazardous organic solvents, and easy workup.
- Kiyani, Hamzeh,Ghorbani, Fatemeh
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p. 6831 - 6844
(2016/08/25)
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- DABCO functionalized dicationic ionic liquid (DDIL): A novel green benchmark in multicomponent synthesis of heterocyclic scaffolds under sustainable reaction conditions
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A novel DABCO functionalized dicationic ionic liquid (DDIL) has been synthesized using diazabicyclo[2,2,2]octane (DABCO), 1,3-dichloro-2-propanol and NaBF4 in acetonitrile. The IL was fully characterized by IR, NMR and mass spectroscopic techniques. The presence of BF4? anion in IL was confirmed by 19F NMR and also supported by mass analysis. The TGA analysis showed that the IL is thermally stable up to 180?°C temperature. We demonstrated that the presence of the tertiary nitrogen sites and hydroxyl group in the DDIL network enhances the overall activity of DDIL. These make them compatible for base catalyzed one pot multicomponent synthesis of ortho-amino carbonitriles and 3-methyl-4-arylmethylene-isoxazol-5(4H)-ones under grinding without solvent. In addition the activity of DDIL was also studied for synthesis of tetrahydrobenzo[b]pyrans under ultrasound irradiation in water. Furthermore the DDIL was easily recoverable and recyclable many times with modest decrease in activity.
- Lohar, Trushant,Kumbhar, Arjun,Barge, Madhuri,Salunkhe, Rajshri
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p. 1102 - 1108
(2016/11/09)
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- Sonochemical synthesis of 3-methyl-4-arylmethylene isoxazole-5(4H)-ones by amine-modified montmorillonite nanoclay
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Ultrasound irradiation was applied for the rapid and clean synthesis of 3-methyl-4-arylmethylene isoxazole-5(4H)-ones through condensation of hydroxylamine hydrochloride, ethyl acetoacetate and benzaldehyde derivatives. This methodology was effectively ca
- Safari, Javad,Ahmadzadeh, Majid,Zarnegar, Zohre
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- Fruit juice of Citrus limon as a biodegradable and reusable catalyst for facile, eco-friendly and green synthesis of 3,4-disubstituted isoxazol-5(4H)-ones and dihydropyrano[2,3-c]-pyrazole derivatives
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Abstract: Fruit juice of Citrus limon (lemon juice) has been utilized as a natural and renewable catalyst for the green and environmentally friendly preparation of 3,4-disubstituted isoxazol-5(4H)-one derivatives and 6-amino-1,4-dihydropyrano[2,3-c]-pyraz
- Vekariya, Rajesh H.,Patel, Kinjal D.,Patel, Hitesh D.
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p. 7559 - 7579
(2016/09/20)
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- Phthalimide-N-oxyl salts: Efficient organocatalysts for facile synthesis of (Z)-3-methyl-4-(arylmethylene)-isoxazole-5(4H)-one derivatives in water
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Green and simple protocols have been developed for the synthesis of (Z)-3-methyl-4-(arylmethylene)isoxazole-5(4H)-one derivatives in the presence of tetrabutylammonium or potassium salts of phthalimide-N-oxyl, as transition metal-free catalysts, through t
- Dekamin, Mohammad G.,Peyman, S. Zahra
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p. 445 - 450
(2016/02/16)
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- 2-Hydroxy-5-sulfobenzoic acid: An efficient organocatalyst for the three-component synthesis of 1-amidoalkyl-2-naphthols and 3,4-disubstituted isoxazol-5(4H)-ones
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2-Hydroxy-5-sulfobenzoic acid (2-HSBA) efficiently catalyzed the one-pot three-component synthesis of a wide variety of 1-amidoalkyl-2-naphthols and 3,4-disubstituted isoxazol-5(4H)-ones. The three-component process of substituted benzaldehydes, 2-naphthol, and amides (benzamide and acetamide) or urea occur using 10 mol% of 2-HSBA as an organocatalyst under solvent-free reaction conditions (SFRCs) at 100 °C. It was also found that the best results for the preparation of 3,4-disubstituted isoxazol-5(4H)-ones were achieved using 15 mol% of 2-HSBA under aqueous conditions at room temperature. The reactions are easy to do and were completed within 3-25 min (for amidoalkyl naphthols), and 70-120 min (for 3,4-disubstituted isoxazol-5(4H)-ones), while the expected products were obtained in 82-97 % yields. The catalyst can be recovered and reused several times in the template reactions. This procedure offers the advantages of convenience, simple operational procedure, cost-effectiveness, no use of hazardous organic solvents, and the commercial availability of the catalyst.
- Kiyani, Hamzeh,Darbandi, Hassan,Mosallanezhad, Asiyeh,Ghorbani, Fatemeh
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p. 7561 - 7579
(2015/02/19)
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- Boric acid-catalyzed multi-component reaction for efficient synthesis of 4H-isoxazol-5-ones in aqueous medium
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Abstract The one-pot three-component reaction of aryl aldehydes with hydroxylamine hydrochloride and ethyl 3-oxobutanoate/ethyl 4-chloro-3-oxobutanoate/ethyl 3-oxo-3-phenylpropanoate in the presence of boric acid, H3BO3, in water lea
- Kiyani, Hamzeh,Ghorbani, Fatemeh
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p. 2653 - 2664
(2015/04/27)
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- An Efficient Synthesis of 4-Arylmethylidene-3-substituted-Isoxazol-5(4H)-ones in Aqueous Medium
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A series of 4-arylmethylidene-3-substituted-isoxazol-5(4H)-ones were efficiently synthesized by eco-benign, one pot uncatalyzed reaction of β-keto-ester, hydroxylamine hydrochloride, and aromatic aldehyde with electron donating substituent in water.
- Chavan, Abhijit P.,Pinjari, Avinash B.,Mhaske, Pravin C.
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p. 1911 - 1915
(2015/02/19)
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- Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water
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A variety of 4H-chromenes, benzochromenes, 4,5-dihydropyrano[3,2-c]chromenes, 4H-pyran-3-carboxylates, and 3,4-disubstituted isoxazol-5(4H)-ones have been synthesized in high yields by using potassium hydrogen phthalate (KHP) as an inexpensive, commercially available catalyst. It was found that the three-component tandem reaction enabled synthesis of pyran-annulated heterocycles in water at 50 °C. 3,4-Disubstituted isoxazol-5(4H)-ones were synthesized by use of 10 mol% KHP in water at room temperature. Also, treatment of methylene-containing compounds (malononitrile or ethyl cyanoacetate) with aromatic aldehydes in the presence of 5 mol% KHP resulted in α,β-unsaturated nitriles. The procedure is an easily performed, straightforward method for synthesis of a variety of pyran-annulated compounds, isoxazol-5(4H)-one-containing heterocycles, and Knoevenagel adducts. The reaction is safe, uses mild conditions, and is environmentally benign. Other notable advantages are reuse of the catalyst, no use of hazardous organic solvents, and ease of work-up.
- Kiyani, Hamzeh,Ghorbani, Fatemeh
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p. 7847 - 7882
(2015/02/19)
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- Acetylenes from Aldehydes. Preparation of Ethynylphenols and Phenylacetylenes by Flash Vacuum Pyrolysis of Isoxazolones
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The flash vacuum pyrolysis method of synthesis of acetylenes from aldehydes via isoxazolones is a convenient method for the preparation of a variety of derivatives, including kinetically unstable, sensitive compounds such as the ethynylphenols.
- Wentrup, Curt,Wiedenstritt, Maria,Winter, Hans-Wilhelm
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p. 1233 - 1236
(2015/08/18)
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- One-pot three-component synthesis of 3-methyl-4-arylmethylene-isoxazol- 5(4H)-ones catalyzed by sodium sulfide
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3-Methyl-4-arylmethylene-isoxazol-5(4H)-ones were synthesized by the convenient three-component reaction of ethyl acetoacetate, hydroxylamine hydrochloride, and aromatic aldehydes catalyzed by sodium sulfide in the presence of ethanol at room temperature.
- Liu, Qing,Hou, Xianming
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experimental part
p. 448 - 453
(2012/03/26)
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