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Catalytic Asymmetric Synthesis of Atropisomeric Nitrones: Versatile Intermediate for Axially Chiral Biaryls.

Organic Letters, 2020
A Cu-catalyzed asymmetric ring-opening reaction of five-membered diaryliodonium salts and oximes is introduced. The reactions undergo selective N-arylation of oximes and provide an efficient protocol for the synthesis of atropisomeric nitrones.
Wenjing Guo, J. Gu, Z. Gu
semanticscholar   +1 more source

Nitrones—V

Tetrahedron, 1978
Abstract Reactions of 3,4-dihydroisoquinoline N-oxide ( 1 ) with carbomethoxymethyldiphenylphosphine oxide ( 13 ) and cyanomethyldiphenylphosphine oxide ( 14 ) lead both in 1,2-dimethoxyethane (DME) and in t-BuOH mostly to enamines 6 and 7 respectively.
Eli Breuer, Shmuel Zbaida
openaire   +2 more sources

Substituted α-Phenyl and α-Naphthlyl-N-tert-butyl Nitrones: Synthesis, Spin-Trapping and Neuroprotection Evaluation.

Journal of Organic Chemistry, 2020
New derivatives of α-phenyl-N-tert-butyl nitrone (PBN) bearing a hydroxyl, an acetate or an acetamide substituent on the N-tert-butyl moiety and para-substituted phenyl or naphthlyl moieties were synthesized.
Anaïs Deletraz   +7 more
semanticscholar   +1 more source

Cyclic nitrones. I. Reactions of α-keto nitrones at nitrone carbon

Australian Journal of Chemistry, 1967
The chemistry of 3,4,5,6-tetrahydro-3-oxopyridine 1-oxides has been studied with respect to: reaction with hydrazine-the 6,6-dimethyl compound (IV) gave a hydrazone (VII) by ring contraction following initial attack at C 2; (ii)(ii) 2-arylation with diazonium salts, e.g.
L Subrahmanyan, Rfc Brown, CP Whittle
openaire   +2 more sources

Nitrones and oxaziridines. VIII. Cycloaddition reactions of nitrones with isothiocyanates

Australian Journal of Chemistry, 1973
Whereas nitrones undergo cycloaddition to the C=N double bond of phenyl isothiocyanate, predominant addition to the C=S double bond of substituted phenyl isothiocyanates, methyl isothiocyanate and benzoyl isothiocyanate occurs. However, these cycloadducts are not stable but undergo fragmentation usually with the formation of thioamides and isocyanates.
Dsc Black, Keith G. Watson
openaire   +2 more sources

Nitrones. Part III. Photolysis of cyclic nitrones

Journal of the Chemical Society C: Organic, 1966
Ultraviolet irradiation of 2-substituted 1-pyrroline 1-oxides yielded corresponding bicyclic oxaziridines. Prolonged irradiation of the 3,3,5-trimethyl-6-oxa-1-azabicyclo[3,1,0]hexane gave an N-acetylazetidine and a pyrroline. Acid hydrolyses of 2,2,5- and 3,3,5-trimethyl-6-oxa-1-azabicyclo[3,1,0]hexane yielded acetonylacetone and 3,3-dimethylpentan-5 ...
L. S. Kaminsky, M. Lamchen
openaire   +2 more sources

C−H Reactivity of the α‐Position in Nitrones and Nitronates

Advanced Synthesis & Catalysis, 2019
AbstractThe review summarizes the chemistry of nitrones and nitronates in the context of the C−H reactivity of their α‐carbon atoms. Electrophilic, nucleophilic and radical reactions leading to functionalization of the α‐position are described. Examples of the application of these processes in total synthesis are outlined.magnified image
Alexey Yu. Sukhorukov   +1 more
openaire   +2 more sources

Cycloadditions of Trans‐Cyclooctenes and Nitrones as Tools for Bioorthogonal Labelling

ChemBioChem, 2020
Trans‐cyclooctenes (TCOs) represent interesting and highly reactive dipolarophiles for organic transformations including bioorthogonal chemistry. Herein we show that TCOs react rapidly with nitrones and that these reactions are bioorthogonal.
Kaitlyn D. Margison   +3 more
semanticscholar   +1 more source

Studies on the chemistry of the chiral nitronic acid and nitronic esters

Tetrahedron: Asymmetry, 1997
Abstract Some new chemistry of the chiral nitronic acid and nitronic esters is described. Conversions with retention of configuration are found among the chiral nitronic acid, oxime, nitronic esters and O -alkyloximes. α,β-Elimination reactions of nitronic esters are observed for the first time. Novel and enantiopure chiral bisheterocyclic compounds
Cheng-Lie Yin, Fu-An Kang
openaire   +2 more sources

Eu(OTf)3-Catalyzed Formal Dipolar [4π + 2σ] Cycloaddition of Bicyclo-[1.1.0]butanes with Nitrones: Access to Polysubstituted 2-Oxa-3-azabicyclo[3.1.1]heptanes.

Angewandte Chemie
Herein, we have synthesized multifunctionalized 2-oxa-3-azabicyclo[3.1.1]heptanes, which are considered potential bioisosteres for meta-substituted arenes, through Eu(OTf)3-catalyzed formal dipolar [4π+2σ] cycloaddition of bicyclo[1.1.0]butanes with ...
Jian Zhang   +4 more
semanticscholar   +1 more source

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