23244-46-4Relevant academic research and scientific papers
Facile and expedient synthesis of α,β-unsaturated isoxazol-5(4H)-ones under mild conditions
Ghorbani, Fatemeh,Kiyani, Hamzeh,Pourmousavi, Seied Ali
, p. 943 - 959 (2019/11/13)
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.].
Enantioselective Synthesis of Functionalized Diazaspirocycles from 4-Benzylideneisoxazol-5(4H)-one Derivatives and Isocyanoacetate Esters
Martínez-Pardo, Pablo,Laviós, Adrián,Sanz-Marco, Amparo,Vila, Carlos,Pedro, José R.,Blay, Gonzalo
, p. 3564 - 3569 (2020/07/24)
Enantioenriched spirocyclic compounds bearing three contiguous stereocenters and high functionalization were obtained through a formal [3+2] cycloaddition reaction catalyzed by a cooperative system. The spiro compounds were synthesized from 4-arylideneisoxazol-5-ones and isocyanoacetate esters using a bifunctional squaramide/Br?nsted base organocatalyst derived from a Cinchona alkaloid and silver oxide as Lewis acid. This method afforded two out of the four possible diastereomers with good yields and high enantiomeric excess for both diastereomers. (Figure presented.).
One-pot green synthesis of isoxazol-5(4H)-one derivatives using Dowex1-x8OH in water
Setamdideh, Davood
, p. 971 - 978 (2016/11/09)
4-(Arylmethylidene)-3-methylisoxazol-5(4H)-ones and 4-(arylmethylidene)-3-phenylisoxazol-5(4H)-ones were synthesized in a one-pot three-component procedure in the presence of Dowex1-x8OH as catalyst in water. The products were obtained in high yields (90-
Regioselective catalytic asymmetric C-alkylation of isoxazolinones by a base-free palladacycle-catalyzed direct 1,4-addition
Hellmuth, Tina,Frey, Wolfgang,Peters, Ren
, p. 2788 - 2791 (2015/03/04)
Isoxazolinones constitute a class of heterocycles utilized for the development of novel drug candidates. The cyclic oxime ester motif is also synthetically useful as it contains functional handles which have previously been used to provide access to an assortment of valuable compound classes not easily accessible by alternative approaches. However, asymmetric methods towards isoxazolinones are notoriously scarce. Herein we report the first catalytic asymmetric alkylations of isoxazolinones forming all-C-substituted quaternary stereocenters. The present studies were driven by the question of how to control the regioselectivity in the competition of different nucleophilic positions. The investigation of a direct 1,4-addition uncovered that a sterically demanding palladacycle catalyst directs the reactivity in the absence of a base nearly exclusively to the nucleophilic C atom, while at the same time it allows for high enantioselectivity and TONs up to 1900.
An easy protocol for the domino synthesis of diversely functionalized spirocarbocycles and their biological evaluation
Kiruthika, Selvarangam E.,Perumal, Paramasivan T,Balachandran,Ignacimuthu
, p. 177 - 185 (2016/02/18)
A base-catalysed domino reaction for the synthesis of spirocarbocycles in excellent yields using chalcones and vinyl malononitriles is reported. This consists of a series of steps including Knoevenagel condensation followed by intermolecular vinylogous Mi
New pathway to pyrrolidinones and pyrrolizidinones using aryl aldehydes, 3-phenyl-5-isoxazolone and secondary amino acids
Lakshmi, Neelakandan Vidhya,Perumal, Paramasivan T.
, p. 1817 - 1820 (2013/04/23)
A novel and efficient approach to pyrrolidinones and pyrrolizidinones via a one-pot multicomponent reaction of aryl aldehydes, 3-phenyl-5-isoxazolone, sarcosine and l-proline, respectively in methanol under reflux condition is reported.
Nano Fe2O3, clinoptilolite and H3PW12O40 as efficient catalysts for solvent-free synthesis of 5(4H)-isoxazolone under microwave irradiation conditions
Fozooni, Samieh,Hosseinzadeh, Nasrin Gholam,Hamidian, Hooshang,Akhgar, Mohammad Reza
, p. 1649 - 1655 (2013/10/22)
A quick and solvent-free approach involving the exposure of neat reactants to microwave irradiation in conjunction with the use of clinoptilolite, H3PW12O40 and Fe2O3 nanoparticle catalysts is described. In this work, condensation of hydroxylamine hydroch
Fast and efficient synthesis of 4-arylidene-3-phenylisoxazol-5-ones
Mirzazadeh, Maryam,Mahdavinia, Gholam Hossein
, p. 425 - 429 (2012/05/20)
A convenient and easy synthesis of 4-arylidene-3-phenylisoxazol-5-ones by the three-component reaction of hydroxylamine, ethyl benzoylacetate and aromatic aldehydes in the presence of DABCO in refluxing ethanol is reported.
The convenient synthesis of 4-arylmethylidene-4,5-dihydro-3-phenylisoxazol- 5-ones
Ablajan, Keyume,Xiamuxi, Hainimu
experimental part, p. 151 - 154 (2012/01/03)
4-Arylmethylidene-4,5-dihydro-3-phenylisoxazol-5-ones were synthesized by the convenient three-component reaction of ethyl benzoylacetate, hydroxylamine and aromatic aldehydes in the presence of pyridine. The target compounds were also obtained by the rea
Gold-catalyzed cyclization and subsequent arylidene group transfer of O-propioloyl oximes
Nakamura, Itaru,Okamoto, Masashi,Terada, Masahiro
supporting information; experimental part, p. 2453 - 2455 (2010/07/05)
Gold-catalyzed cyclizations of O-propioloyl oximes via C-N bond formation followed by arylidene group transfer were successfully carried out to afford the corresponding 4-arylideneisoxazol-5(4H)-ones in good to excellent yields. As an example, (E)-benzaldehyde O-3-phenylpropioloyl oxime (1a) was reacted in acetonitrile at 25 °C in the presence of Au(PPh3)NTf2 (5 mol %) to give 4-benzylidene-3-phenylisoxazol-5(4H)-one (2a) in 90% yield. On the basis of crossover experiments, the arylidene "migration" was shown to proceed in an intermolecular manner.
