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<i>One-pot</i> dearomatizative telescoped addition of <i>C</i>-nucleophiles to fluorinated 1,2,4-oxadiazoles followed by regioselective <i>N</i>-functionalization.

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Castiglione D   +9 more
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Organocatalyzed nucleophilic addition of pyrazoles to 2H-azirines: asymmetric synthesis of 3,3-disubstituted aziridines and kinetic resolution of racemic 2H-azirines

Chemical Communications, 2016
An asymmetric nucleophilic addition of pyrazoles to 2H-azirines via organocatalytic kinetic resolution afforded chiral aziridines and azirines simultaneously.
Dong An, Suoqin Zhang
exaly   +3 more sources

2H-Azirines as Synthetic Tools in Organic Chemistry

European Journal of Organic Chemistry, 2001
The versatility and the high synthetic potential including the asymmetric syntheses of 2H-azirines as valuable precursors for the preparation of a wide range of polyfunctional acyclic and cyclic compounds, is discussed.
Francisco Palacios   +1 more
exaly   +2 more sources

2H-Azirines in medicinal chemistry

Chemistry of Heterocyclic Compounds, 2021
The review presents an analysis of studies published in the period 1971–2020 devoted to examination of the biological activity of natural and synthetic 2H-azirine derivatives, their use for bioconjugation, as well as search for some new synthetic methods of structural modification of azirines with the aim of improving their biological activity.
Pavel А. Sakharov   +2 more
openaire   +1 more source

Exploiting 2-Halo-2H-Azirine Chemistry

Current Organic Synthesis, 2004
H-Azirines are the smallest unsaturated heterocyclic compounds containing nitrogen. Despite their strain many stable azirines are known. Due to the high reactivity 2H-azirines have been explored extensively for various synthetic purposes. The ring system occurs naturally in the antibiotics azirinomycin, isolated from Streptomyces auras cultures ...
Teresa Pinho e Melo, Antonio Gonsalves
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Alkylation et silylation de 2h-azirines

Tetrahedron Letters, 1985
Resume Alkylation and silylation of 2H-azitines are reported. Methylation of lithiated azirines is always observed at the carbon atom. N- or C-silytated azirines can be obtained depending on the silyl reagents or substrates.
P.F. Belloir   +4 more
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Electronic structures of vinylazide, vinylnitrene and 2H-azirine. Mechanism of the reaction from vinylazide to 2H-azirine

Tetrahedron, 1984
Abstract The mechanism of the conversion of vinylazides into 2H-azirines is examined by use of ab initio MO calculations. It is ascertained that vinylnitrenes have very weak bonds between the vinylazides and nitrogen molecule parts. It seems to decompose readily into the two fragments.
Tokio Yamabe   +5 more
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Conical intersections and photoreactions of 2H-azirines

Chemical Physics, 2000
Abstract CASSCF calculations were performed on the nπ * - and ππ * -excited states of 2 H -azirine as well as some alkyl-substituted 2 H -azirines. An S 1 /S 0 conical intersection (CI) was located, through which a direct formation of nitrile ylide can occur.
Christian Bornemann, Martin Klessinger
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Thermal rearrangements of 2,3-diphenyl-2H-azirine

Journal of the Chemical Society, Perkin Transactions 1, 1973
Heating 2,3-diphenyl-2H-azirine in a sealed tube at 250 °C for 3 h yields 2-phenylindole, 2,3,4,5-tetraphenylpyrrole, 2,4,5-triphenylimidazole, and 1-benzyl-2,4,5-triphenylimidazole as major products, with tetraphenylpyrazine, tetraphenylpyrimidine, pentaphenylpyridine, benzonitrile, benzamide, and stilbene being produced in smaller yield.
John H. Bowie, Brian Nussey
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Photocycloaddition reactions of a bis-2H-azirine

Journal of the Chemical Society, Chemical Communications, 1977
Irradiation of 3,3′-(2,2′-biphenylene)bis-(2H)-azirine with electron-deficient dipolarophiles gives cycloadducts derived from a transient azabicyclo[3.1.0]hexene intermediate.
Albert Padwa, Hao Ku
openaire   +1 more source

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