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Copper-catalyzed pyrrole synthesis from 3,6-dihydro-1,2-oxazines

open access: yesCopper-catalyzed pyrrole synthesis from 3,6-dihydro-1,2-oxazines
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PTP-1B inhibitors: Cyclopenta[d][1,2]-oxazine derivatives

Bioorganic & Medicinal Chemistry Letters, 2006
A series of novel cyclopenta[d][1,2]-oxazine derivatives was prepared and evaluated for their inhibitory activity toward protein tyrosine phosphatase 1B (PTP-1B). Compound 6s was found to be an inhibitor of PTP-1B with nanomolar IC(50) value and high level of selectivity over other recombinant phosphatases.
Sung Yun, Cho   +13 more
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3,6-Dihydro-2H-1,2-oxazines (microreview)

Chemistry of Heterocyclic Compounds, 2016
Recent synthetic methods towards 3,6-dihydro-2H-1,2-oxazines are reviewed. This Focus covers selected examples on the synthesis of 3,6-dihydro-2H-1,2-oxazines that can be grouped in the following categories: (4+2) cycloadditions, tandem reactions, formal (3+3) cycloadditions, and ring-closing metathesis.
Greta Utecht, Marcin Jasiński
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ChemInform Abstract: 1,2‐OXAZINE CHEMISTRY PART 1, SYNTHETIC APPROACHES TO TETRAHYDRO‐1,2‐OXAZINES

Chemischer Informationsdienst, 1974
AbstractDurch Umsetzung entsprechender Dibromide (I) mit dem Hydroxyurethan (II) im Verhältnis l 23 werden die Titelverbindungen (III) dargestellt; im Falle der cis‐ bzw. trans‐Verbindungen (IIIb) bleibt die Stereochemie der entsprechenden meso‐ bzw. racemischen Ausgangsverbindungen (I) erhalten.
F. G. RIDDELL, D. A. R. WILLIAMS
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Amino sugars and their mimetics via 1,2-oxazines

Chem. Soc. Rev., 2010
This tutorial review covers recent research from our laboratory towards the synthesis of amino sugars and related carbohydrate mimetics employing 1,2-oxazines as crucial intermediates. The synthesis of new dideoxyamino carbohydrate derivatives, C2-branched 4-amino sugars and their mimetics, as well as sialic acid analogues, has been developed during ...
Fabian, Pfrengle, Hans-Ulrich, Reissig
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ChemInform Abstract: SYNTHESIS WITH 1,2‐OXAZINES. I. A SYNTHESIS OF 4,5‐DIHYDRO‐6H‐1,2‐OXAZIN‐6‐ONE DERIVATIVES

Chemischer Informationsdienst, 1977
AbstractDie aus den Carbonsäuren (I) über die entsprechenden Säurechloride erhältlichen N‐Acyloxycarbamate (II) geben bei Cyclisierung mit Trifluoressigsäure bzw. p‐Toluolsulfonsäure die Oxazinone (III).
B. HARDEGGER, S. SHATZMILLER
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1,2‐oxazine chemistry. V—vicinal, allylic and homoallylic coupling constants in the 3,6‐dihydro‐1,2‐oxazine ring

Organic Magnetic Resonance, 1974
AbstractThe 1H NMR spectra of thirteen dihydro‐1,2‐oxazine derivatives are reported. Spin decoupling allows analysis of the spectra, features of which include homoallylic couplings of +2 to +2·5 Hz, allylic couplings of −1·5 to −1·7 Hz and vicinal couplings across sp2 to sp3 carbon–carbon bonds of +2·9 to +3·7 Hz.
F. G. Riddell, H. Labaziewicz
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Nitrogen inversion in 3,6‐dihydro‐1,2‐oxazines

Organic Magnetic Resonance, 1980
AbstractThe nitrogen inversion barriers of nine 3,6‐dihydro‐1,2‐oxazines are discussed. Polar solvents were found to increase the nitrogen inversion barriers which, in turn, decrease with increasing size of the N‐substituent.
Henryk Labaziewicz, Frank G. Riddell
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