1137-96-8Relevant academic research and scientific papers
Selective reductive coupling of nitro compounds with aldehydes to nitrones in H2 using carbon-supported and -decorated platinum nanoparticles
Cisneros, Larisha,Serna, Pedro,Corma, Avelino
, (2014)
Nitrones were synthesized in high yields directly from nitro compounds, aldehydes, and H2 using carbon-decorated platinum nanoparticles. The high selectivity for nitrone synthesis contrasts that of common supported metal catalysts and correspon
Urea-catalyzed construction of oxazinanes
Hardman, Andrea M.,So, Sonia S.,Mattson, Anita E.
, p. 5793 - 5797 (2013)
Highly functionalized oxazinanes are efficiently prepared through urea-catalyzed formal [3 + 3] cycloaddition reactions of nitrones and nitrocyclopropane carboxylates. The reaction system is general with respect to both the nitrocyclopropane carboxylates and nitrones enabling the preparation of a large family of oxazinanes, typically in high yield. This method affords access to enantioenriched oxazinane products through chirality transfer from enantioenriched nitrocyclopropane carboxylates.
Strain-Release Driven Cycloadditions for Rapid Construction of Functionalized Pyridines and Amino Alcohols
Clementson, Sebastian,Radaelli, Alessio,Fjelbye, Kasper,Tanner, David,Jessing, Mikkel
, p. 4763 - 4766 (2019)
This paper describes the development of a new variant of stereoselective strain-release driven reactions (formal homo [3 + 2] dipolar cycloadditions) which utilize housane (1) to construct functionalized amino alcohols and pyridine-substituted cyclopentanes in two to three steps from simple and easily available building blocks (nitrones and pyridine N-oxides respectively).
Differences among the mechanisms of reaction of phenylhydroxylamine with various carbonyl compounds
Brighente,Menegatti,Yunes
, p. 453 - 459 (2000)
In order to obtain a better knowledge of the special behavior of phenylhydroxylamine as a nucleophile, the mechanism of its reaction with 2,6-dichlorobenzaldehyde, norcamphor, and cyclohexanone, and also the hydrophobic effect on its reaction with 2,6-dichlorobenzaldehyde and benzaldehyde, was studied. The results led us to assume that the planar molecule of phenylhydroxylamine should be placed parallel to the planar molecule of benzaldehyde in order to permit the attack of the lone electron pair of the nitrogen on the carbonyl group, forming, together with a hydrogen bond between the hydroxyl group and the carbonylic oxygen atom, a packed preassociation complex. This mechanism is not observed in the case of norcamphor or 2,6-dichlorobenzaldehyde due to the steric hindrances produced by the lack of planarity of these molecules.
Synthesis of 2′,3′,4′-triaryl-5,6-dihydro-8H-spiro[indolizine-7,5′-isoxazolidin]-8-ones via 1,3-dipolar cycloaddition reaction involving (Z)-C-aryl-N-phenylnitrones
Li, Xiaofang,Li, Youfeng,Tang, Jin
, (2020)
[Figure not available: see fulltext.] The 1,3-dipolar cycloaddition of C-aryl-N-phenylnitrones to 7-arylmethylidene-6,7-dihydroindolizin-8(5H)-ones afforded novel 2′,3′,4′-triaryl-5,6-dihydro-8H-spiro[indolizine-7,5′-isoxazolidin]-8-ones in moderate yield
High diastereoselectivity induced by intermolecular hydrogen bonding in [3?+?2] cycloaddition reaction: experimental and computational mechanistic approaches
Y?ld?r?m, Ayhan,Kaya, Yunus
, (2017)
A diastereoselective [3?+?2] cycloaddition of N-aryl substituted maleimides with N,α-diphenyl nitrone possessing 11-hydroxyundecyloxy as a flexible substituent was performed. Experimental and comprehensive mechanistic density functional theory studies reveals that intermolecular H-bonding and steric repulsive interaction predominate exo-Z and exo-E cycloaddition transition states, respectively. The reaction proceeded smoothly depending on the reactants and gave a good yield of (syn) cis-isoxazolidine or (anti) trans-isoxazolidine as a single diastereomer.
Facile approach to alkaloid-like 6/6/5/5-tetracyclic spiroheterocycles via 1,3-dipolar cycloaddition reaction of fused 1H-pyrrole-2,3-diones with nitrones
Stepanova, Ekaterina E.,Dmitriev, Maksim V.,Maslivets, Andrey N.
, (2020)
A facile synthetic approach towards 6/6/5/5-tetracyclic spiroheterocycles has been developed from the highly diastereoselective 1,3-dipolar cycloaddition reaction of [e]-fused 1H-pyrrole-2,3-diones with nitrones. The described novel heterocyclic systems are heteroanalogs of cytotoxic alkaloids, kibalaurifoline and gitingensine. The developed reaction represents the first example of involvement of 1H-pyrrole-2,3-diones fused at [e]-side in a 1,3-dipolar cycloaddition reaction.
Aerobic oxidation of hydroxylamines with nanoporous gold catalyst as an efficient synthetic method of nitrones Dedicated to Professor Jiro Tsuji on the occasion of his receipt of the 2014 Tetrahedron Prize
Yudha S, Salprima,Kusuma, Indra,Asao, Naoki
, p. 6459 - 6462 (2015)
Abstract A facile preparation of nitrones has been achieved by use of unsupported nanoporous gold (AuNPore) as a heterogeneous catalyst through aerobic oxidation of N,N-disubstituted hydroxylamines with molecular oxygen as an oxidizing agent under mild conditions. A variety of amines were oxidized to the corresponding nitrones in high chemical yields. The catalyst is robust enough to be reused without leaching.
Selective oxidation of N-alkyl imines to oxaziridines using UHP/maleic anhydride system
Damavandi, Jafar Asgarian,Karami, Bahador,Zolfigol, Mohammad Ali
, p. 933 - 934 (2002)
Several structurally differentiated N-alkyl imines were oxidized to their corresponding oxaziridines using UHP/maleic anhydride system. Oxidation reaction was performed under mild conditions and oxaziridines were obtained in good to excellent yields.
Polyfunctionalized biaryls accessed by a one-pot nucleophilic aromatic substitution and sigmatropic rearrangement reaction cascade under mild conditions
Liang, Dong-Dong,Guo, Shen-Yi,Tong, Shuo,Wang, Mei-Xiang
supporting information, (2021/02/09)
A practical synthetic method has been developed for polyfunctionalized biaryls based on a facile one-pot nucleophilic aromatic substitution (SNAr) reaction and [5,5]- or [3,3]-sigmatropic rearrangement reaction cascade. Under mild basic conditions, N-arylhydroxylamines reacted with o-activated fluoro (het)arenes to form N,O-diarylhydroxylamine intermediates which underwent spontaneously selective [5,5]-sigmatropic rearrangement reaction to produce diverse functionalized 4-amino-4′-hydroxy-1,1′-biaryls. A sequential SNAr reaction and [3,3]-sigmatropic rearrangement took place between N-arylhydroxylamines and 2-fluoropyridine derivatives or 4-fluorobenzonitrile to afford functionalized 2-amino-2′-hydroxy-1,1′-biaryls. As invaluable and unique building blocks, the resulting biaryls were applied in the straightforward synthesis of N2,O2-coronarene, carbazole, aza- and diaza carbazole derivatives.
