- A facile and new method for the synthesis of α-aryl-N-methylnitrones in solvent-free media using silica gel-NaOH
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Substituted α-aryl-N-methylnitrones are prepared by the condensation reaction of N-methylhydroxylamine hydrochloride and benzaldehydes in solvent-free media using silica-gel-NaOH catalyst system. The yields are excellent regardless of the electron-donatin
- Alavi Nikje,Bigdeli,Imanieh
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- Cucurbit[7]uril as a catalytic nanoreactor for one-pot synthesis of isoxazolidines in water
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The main objective of supramolecular chemistry is to mimic the macrosystems present in nature, a goal that fits perfectly with the green chemistry guidelines. The aim of our work is to use the hydrophobic cavity of cucurbit[7]uril (CB[7]) to mimic nature
- Floresta, Giuseppe,Gentile, Davide,Mineo, Placido G.,Nicosia, Angelo,Patamia, Vincenzo,Rescifina, Antonio
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supporting information
p. 1194 - 1203
(2020/02/22)
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- A green synthesis of nitrones in glycerol
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Abstract: An eco-friendly and efficient synthesis of nitrones is presented by condensation of an equimolar amount of aldehydes and N-substituted hydroxylamine hydrochlorides in glycerol as a recyclable solvent-catalyst. This novel protocol provides rapid and mild access to a series of nitrone derivatives in good to excellent yields in the absence of catalyst and base. Graphic abstract: SYNOPSIS In this study, a base-free protocol by using glycerol as the solvent-catalyst was applied for an eco-friendly synthesis of nitrones from the condensation of aldehydes and N-substituted hydroxylaminehydrochlorides.[Figure not available: see fulltext.].
- Shariatipour, Monire,Jadidinejad, Masoumeh,Heydari, Akbar
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- Synthesis of 1,2,4-oxadiazolidines via [3+2] cycloaddition of nitrones with carbodiimides
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An efficient [3+2] cycloaddition of nitrones and carbodiimides has been developed. This 1,3-dipolar cycloaddition features high regioselectivity, mild and metal-free conditions, excellent functional group compatibility, and a broad substrate scope. The X-ray structures of two regio-isomers confirmed the regioselectivity of this transformation.
- Chen, Yuan,Fuyue, Liuting,Wang, Gangqiang,Wang, Hang,Lu, Chun,Guo, Haibing,St. Amant, Chiara,Sun, Shaofa,Xing, Yalan
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supporting information
p. 4329 - 4332
(2019/03/19)
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- BPh3-Catalyzed [2+3] Cycloaddition of Ph3PCCO with Aldonitrones: Access to 5-Isoxazolidinones with Exocyclic Phosphonium Ylide Moieties
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A method for the generation of 5-isoxazolidinones with exocyclic phosphonium ylide functionalities via [2+3] cycloaddition of Ph3PCCO and aldonitrones has been developed and applied in the synthesis of 4-alkylidene-5-isoxazolidinones via Wittig olefination. The reaction proceeds by BPh3 catalysis under mild conditions and with a broad substrate scope. A reaction pathway involving the activation of the aldonitrone via interactions with the Lewis acid BPh3 is proposed.
- Brar, Amandeep,Unruh, Daniel K.,Ling, Natalie,Krempner, Clemens
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p. 6305 - 6309
(2019/08/20)
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- Accessing benzooxadiazepines: Via formal [4 + 3] cycloadditions of aza- o -quinone methides with nitrones
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An unprecedented and efficient [4 + 3] cycloaddition of N-(ortho-chloromethyl)aryl amides with nitrones has been developed. This approach provides easy access to a series of seven-membered benzooxadiazepine derivatives in good to excellent yields (up to 99% yield) under mild reaction conditions.
- Zheng, Yong-Sheng,Tu, Liang,Gao, Li-Mei,Huang, Rong,Feng, Tao,Sun, Huan,Wang, Wen-Xuan,Li, Zheng-Hui,Liu, Ji-Kai
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p. 2639 - 2642
(2018/04/27)
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- A highly diastereoselective [3+3] annulation reaction of aza-oxyallyl cations and nitrones
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An efficient synthesis of 1,2,4-oxadiazinan-5-ones via [3+3] cycloaddition of in situ generated aza-oxyallyl cations with nitrones has been developed. The protocol features easy operation, excellent yields, excellent diastereo-control, broad substrate sco
- Chen, Rongxing,Sun, Shaofa,Wang, Gangqiang,Guo, Haibin
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supporting information
p. 1916 - 1920
(2018/04/19)
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- Crystal and molecular structure studies of (Z)-N-methyl-C-4-substituted phenyl nitrones by XRD, DFT, FTIR and NMR methods
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(Z)-N-methyl-C-4-substituted phenyl nitrones –O+N(Me)=C(H)R (Z-2a R = 4-ClC6H4, Z-2b R = 4-NO2C6H4, Z-2c R = 4-CH3OC6H4) were synthesized and cha
- Lasri, Jamal,Eltayeb, Naser Eltaher,Haukka, Matti,Alghamdi, Yousef
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- γ-Cyclodextrin as a Catalyst for the Synthesis of 2-Methyl-3,5-diarylisoxazolidines in Water
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A green and efficient 1,3-dipolar cycloaddition of nitrones with different styrenes and cinnamates using a catalytic amount of γ-cyclodextrin (γ-CD) in water has been developed to give substituted isoxazolidines. γ-CD was found to be highly efficacious in
- Floresta, Giuseppe,Talotta, Carmen,Gaeta, Carmine,De Rosa, Margherita,Chiacchio, Ugo,Neri, Placido,Rescifina, Antonio
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p. 4631 - 4639
(2017/05/12)
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- Synthesis and application of phenyl Nitrone derivatives as acidic and microbial corrosion inhibitors
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Nitrone has drawn great attention due to its wide applications as a 1,3-dipole in heterocyclic compounds synthesis and the bioactivities. With the special structure, nitrone can also be used as ligand in inorganic chemistry. Based on the current research,
- Chen, Shijun,Zhao, Kang,Chen, Gang
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- Fast method for synthesis of alkyl and aryl-N-methylnitrones
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A simple, fast, efficient and eco-friendly procedure was developed for the synthesis of alkyl and aryl-N-methylnitrones. The corresponding nitrones of aromatic aldehydes, aliphatic aldehydes and alicyclic carbonyl compounds were prepared from N-methylhydr
- Yavuz, Serkan,Ozkan, Hamdi,Colak, Naki,Yildirir, Yilmaz
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experimental part
p. 6677 - 6683
(2011/10/31)
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- 1,3-Dipolar cycloadditions. Part XVII: Experimental and theoretical spectroscopic investigations of C-aryl-N-methyl nitrones
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Detailed experimental and theoretical spectroscopic studies of C-aryl-N-methyl nitrones have been reported. The optimized geometries have been calculated by DFT/B3LYP level of theory with 6-31+G(d,p) basis set. The theoretically computed frontier orbital
- Acharjee, Nivedita,Banerji, Avijit,Banerjee, Manas,Das, Tapas K.
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body text
p. 1627 - 1637
(2010/06/17)
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- 1,3-Dipolar cycloadditions. Part-XV: Systematic spectroscopic investigations of C-aryl-N-methylnitrones
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Several C-aryl-N-methylnitrones have been synthesised during the course of our work on 1,3-dipolar cycloadditions. Detailed systematic spectroscopic investigations of all these nitrones have been undertaken. These are reported along with some generalisati
- Banerji, Avijit,Acharjee, Nivedita,Biswas, Pizush Kanti
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scheme or table
p. 63 - 67
(2010/05/02)
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- Solvent-free synthesis of nitrones in a ball-mill
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Various C-aryl and C-alkyl-nitrones were synthesized within 0.5-2 h via condensation of an equimolar amount of aldehydes and N-substituted-hydroxylamines under solvent-free conditions in?a ball-mill apparatus. Reactions can be performed without the need of excluding air and moisture and yields the expected products with no need for further purification. The study has been complemented by Differential Scanning Calorimetry (DSC) and solid-state 13C MAS nuclear magnetic resonance experiments. We have also studied the temperature profile during the reaction. A comparative study with the corresponding solvent-free microwave activated reaction showed the superiority of the ball-milling method; 31 examples are described, including the synthesis of the anti-aging agent C-phenyl-N-tert-butyl nitrone (PBN) and one of its analogues C-2-pyridyl-N-tert-butylnitrone (2-PyBN).
- Colacino, Evelina,Nun, Pierrick,Colacino, Francesco Maria,Martinez, Jean,Lamaty, Frédéric
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p. 5569 - 5576
(2008/09/21)
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- Exploiting microwave-assisted neat procedures: synthesis of N-aryl and N-alkylnitrones and their cycloaddition en route for isoxazolidines
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Microwave irradiation allows increasing the speed of several reactions and also offers the possibility of eliminating poisoning organic solvents. In this work we report the microwave-assisted neat synthesis of α-phenyl-tert-butylnitrone (PBN) and other alkyl and aryl nitrones and also the rapid synthesis of isoxazolidines resulting from 1,3-dipolar cycloaddition of nitrones to ethyl trans-crotonate.
- Andrade, Marta M.,Barros, Maria Teresa,Pinto, Rui C.
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p. 10521 - 10530
(2008/12/23)
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- Asymmetric 1,3-dipolar cycloaddition reactions of nitrones with (S)-(-)-4-benzyl-N-methacryloyl-2-oxazolidinone
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The [3+2]-nitrone-mediated cycloaddition reaction of (S)-(-)-4-benzyl-N- methacryloyl-2-oxazolidinone has been applied to the synthesis of highly substituted isoxazolidines with controlled stereochemistry. The absolute configuration of the major diastereo
- Tyrrell, Elizabeth,Allen, Jackie,Jones, Keith,Beauchet, Romain
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p. 2393 - 2399
(2007/10/03)
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- Oxidation of secondary amines by molecular oxygen and cyclohexanone monooxygenase
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Cyclohexanone monooxygenase from Acinetobacter calcoaceticus catalyzed the oxidation of tertiary and secondary amines to N-oxides and nitrones, respectively. The formation of a hydroxylamine intermediate was involved with secondary amines as starting substrates.
- Colonna, Stefano,Pironti, Vincenza,Carrea, Giacomo,Pasta, Piero,Zambianchi, Francesca
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p. 569 - 575
(2007/10/03)
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- 1,3-Dipolar cycloadditions: Part VIII1-Microwave irradiation assisted synthesis of N-methyl-C-aryl nitrones
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N-Methyl-C-arylnitrones have been synthesized in very high yields within a few minutes from N-methyl-hydroxylamine hydrochloride and aryl aldehydes in presence of sodium hydrogen carbonate in methylene chloride using the microwave irradiation technique.
- Banerji, Avijit,Biswas, Pizush Kanti,Sengupta, Piyali,Dasgupta, Saugandha,Gupta, Maya
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p. 880 - 881
(2007/10/03)
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- Synthesis of functionalized sulfonamides via 1,3-dipolar cycloaddition of pentafluorophenyl vinylsulfonate
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(Matrix presented) An efficient intermolecular 1,3-dipolar cycloaddition of a variety of nitrones to pentafluorophenyl (PFP) vinylsulfonate is described. The transformation produces stable "reversed" cycloadducts of unprecedented stereo- and regioselectiv
- Caddick, Stephen,Bush, Hannah D.
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p. 2489 - 2492
(2007/10/03)
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- An efficient and rapid chemoselective synthesis of α-Aryl-N-methylnitrones in dry media
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A simple, efficient, and eco-friendly procedure was developed for the condensation of N-methylhydroxylamine hydrochloride with benzaldehydes bearing electron-donating or electron-withdrawing substituents in the presence of powdered molecular sieves (3 A)
- Bigdeli,Nikje
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p. 1547 - 1549
(2007/10/03)
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- Oxidation of N-benzyl-N-methylhydroxylamines to nitrones. A mechanistic study
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Oxidation of various N-(o-, m-, p- substituted benzyl)- N-methylhydroxylamines has been carried out using mercury(II) oxide and p-benzoquinone (p-BQ) as oxidants. Hammett plots have been obtained with negative ρ values, showing the development of a positive centre in the transition state. The unstable E nitrones, which readily isomerize to the more stable Z nitrones, are obtained in appreciable quantities and in some cases as the major product. A considerable deuterium isotope effect is observed in the oxidation process. The overall picture of the mechanistic pathway involves electron transfer from nitrogen to the oxidant followed by hydrogen abstraction.
- Hassan, Azfar,Wazeer, Mohammed I. M.,Ali, Sk. Asrof
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p. 393 - 399
(2007/10/03)
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- Chromium and Tungsten Pentacarbonyl Groups as Reactivity and Selectivity Auxiliaries in Cycloaddition of Alkynyl Fischer Carbene Complexes with N-Alkyl Nitrones
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Alkynyl Fischer carbene complexes were found to undergo chemoselective, regioselective, and rate-enhanced 1,3-dipolar cycloaddition with nitrones to give 2,3-dihydroisoxazole carbene complexes in excellent yields.These alkynyl complexes can serve as synth
- Chan, Kin Shing,Yeung, Ming Lok,Chan, Wai-kin,Wang, Ru-Ji,Mak, Thomas C. W.
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p. 1741 - 1747
(2007/10/02)
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- A Novel Nitrone Cycloaddition/ Rearrangement
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Adamantanone-derived nitrone 4 and some other keto-nitrones, when reacted with aromatic and aliphatic aldehydes in refluxing toluene or tetrahydrofuran, formed the corresponding aldonitrones (Z)-10, the latter arising from the fragmentation of an initially formed 1,4,2-dioxazolidine 6 to adamantan-2-one and an oxaziridine intermediate 11, which then rearranges to (Z)-10.
- Toder, Bruce H.,Mullen, George B.,Georgiev, Vassil St.
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p. 169 - 173
(2007/10/02)
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- An Efficient Method for the Generation of N-Methylnitrones
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N-methylnitrones can be generated in good-to-excellent yields from aldehydes and ketones with a stoichiometric amount of N-methyl-N,O-bis(trimethylsilyl)hydroxylamine under very mild conditions and their formation, involving a bimolecular push-pull type mechanism, is discussed.
- Robl, Jeffrey A.,Hwu, Jih Ru
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p. 5913 - 5916
(2007/10/02)
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- DYNAMIC STEREOCHEMISTRY OF IMINES AND DERIVATIVES. PART 18. PHOTOSYNTHESIS AND PHOTORACEMIZATION OF OPTICALLY ACTIVE OXAZIRIDINES
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Optically active oxaziridines have been synthesized with a maximum optical yield of 31percent by photoisomerization (λ > 300 nm) of achiral aldo- and keto-nitrones in the presence of the chiral solvent (+)-(S) or (-)-(R)-2,2,2-trifluoro-1-phenylethanol.Ph
- Boyd, Derek R.,Campbell, Rose M.,Coulter, Peter B.,Grimshaw, James,Neill, David C.,Jennings, W. Brian
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p. 849 - 856
(2007/10/02)
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