Search results for " molecule"
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PHOSPHORORGANISCHE VERBINDUNGEN 1081DIE SYNTHESE FLUORESZIERENDER UND CHEMOSELEKTIVER REAGENTIEN ZUM GEZIELTEN NACHWEIS UND SCHUTZ BIOLOGISCH WICHTIG…
1984
Abstract Compounds of type A are fluorescent, if the donator groups, like NMe2, OMe, SMe and PR2, and the acceptor groups, like R′P(O)X, SO2R′ and CO2R′, are linked to different nuclei of the naphthalin ring system.
Stereocontrolled synthesis of azeto[2,1-b] quinazolines bearing three stereocenters via the intramolecular [2+2] cycloaddition between ketenimines an…
2004
Abstract A highly stereoselective synthesis of azeto[2,1- b ]quinazolines bearing three stereocenters (C1, C2, and C8) has been achieved via intramolecular [2+2] cycloaddition between ketenimine and imine functions supported on an ortho -benzylic scaffold. An asymmetric center adjacent to the iminic nitrogen atom, the future C8 carbon of the bicyclic product, efficiently controls the absolute configuration of the two new stereogenic carbon atoms of the azetidine ring, C1 and C2.
Ring transformation of furfural into an unusual bicyclic system: Characterisation and dynamic stereochemistry of 6,7-diethoxycarbonyl-6,7-diaza-8-oxa…
1997
Abstract 2-Formylthiophene and 3-formylindole react with diethyl azodicarboxylate to give simple products derived from reactions on the formyl group whereas 2-formylfuran reacts to give the unexpected bicyclic title compound. 1 H and 13 C NMR studies indicate that this compound undergoes a series of three dynamic conformational changes over the temperature range 50 to −90°C which are ascribed to slow rotation about the exocyclic carbamate bonds and hindered bridge inversion.
Auxiliary-controlled stereoselective enolate protonation: Enantioselective synthesis of cis and trans annulated decahydroquinoline alkaloids
1998
Abstract The diastereoselective synthesis of the octahydroquinoline enone precursor of pumiliotoxin C is achieved via tandem Mannich-Michael reaction on N-galactosyl imines. Conjugate cuprate addition to the bicyclic enone stereoselectively forms the trans annulated 4a- epi -pumiliotoxin C skeleton in the presence of the carbohydrate auxiliary, and the cis annulated pumiliotoxin C skeleton in its absence.
Understanding the mechanism of stereoselective synthesis of cyclopentenes via N-heterocyclic carbene catalyzed reactions of enals with enones.
2010
The N-heterocyclic carbene (NHC) catalyzed addition of enals to enones to yield trans-cyclopentenes has been investigated using DFT methods at B3LYP/6-31G** computational level. This NHC catalyzed reaction comprises several steps. The first one is the formation of a Breslow intermediate, which nucleophilically attacks to the conjugated position of the enone to yield an enol-enolate. This second step is responsible for the trans relationship at the final cyclopentene. An intramolecular aldolic condensation allows for the formation of the alkoxy cyclopentane intermediate, that by intramolecular nucleophilic attack on the carbonyl group yields a bicyclic ether. The extrusion of the NHC catalys…
Preparation of dopaminergic N-alkyl-benzyltetrahydroisoquinolines using a 'one-pot' procedure in acid medium.
2000
The preparation of N-methyl-BTHIQ (4) from N-phenylethyl-phenacetamide (1) by cyclization, reduction and N-alkylation in acid medium has been achieved in good yield in a 'one-pot' procedure. Acylation of imine (2) intermediate afforded the Z and E stereoselectivity in the enamide formation. 6-Hydroxy-BTHIQ (7) shows selectivity for D2 dopamine receptors, while its N-methylated homologue (8) displays higher affinities for both D1 and D2 receptor types, with an unexpected increase in D1 dopamine receptor affinity.
The fluxional behaviour of η6(bicyclo[6.2.0]deca-2,4,6-triene) hexacarbonyl diruthenium (Ru-Ru) by 1H and 13C NMR techniques
1977
Abstract The variable temperature 1 H NMR spectra of [Ru 2 (CO) 6 η 6 -C 10 H 12 )] (C 10 H 12 = bicyclo [6.2.0]-deca-2,4,6-triene) shows that this molecule undergoes the fluxional behaviour previously reported for [M 2 (CO) 6 (η 6 -polyolefin)] complexes (M = Fe, Ru) which have in the solid an asymmetric skew-type structure. The use of 13 C NMR techniques, employed for the first time for a diruthenium complex of the above type, allows a comparison of the mechanism of the fluxional process with that of the diiron analog. Although the observed line shape changes of the carbonyl resonances in the two complexes are somewhat different the process are basically the same. In the case of the dirut…
Two-carbon bridge substituted cocaines: enantioselective synthesis, attribution of the absolute configuration and biological activity of novel 6- and…
1999
In an effort to learn more about the general structure-activity relationships of cocaine with the aim to elucidate those structural features that might confer antagonistic properties to such analogues, we describe herein our synthetic efforts to prepare two-carbon bridge functionalized (methoxylated and hydroxylated) analogues. Our approach makes use of a modification of the classical Willstatter synthesis of cocaine: Mannich type cyclization of acetonedicarboxylic acid monomethyl ester with methylamine hydrochloride and 2-methoxysuccindialdehyde in a citrate buffer solution afforded the 6- and 7-substituted 2-carbomethoxy-3-tropinones 3a,b and 4a,b in approximate yields of 64%. Reduction o…
An easy route to 1-germaindenes via a transmetallation zirconiumgermanium reaction
1993
Abstract Several 1-zirconaindenes ( 4 ) have been obtained easily by heating phenylmethylzirconocene with various symmetrical (R R′ CH 3 , C 2 H 5 , n-C 3 H 7 , Si(CH 3 ) 3 and unsymmetrical (R CH 3 , R′ Si(CH 3 ) 3 ) alkynes (RCCR′). Under similar experimental conditions, the ynamine, diethylaminotrimethylsilylethyne, led to a regioselective reaction. From the X-ray structure of the zirconaindene product, the trimethylsilyl group was found close to the zirconium atom. Compounds 4 with germanium tetrachloride afford new 1-germaindenes ( 7 ) characterized by 1 H and 13 C NMR and mass spectrometry, in good yield.
De novo design of protein kinase inhibitors by in silico identification of hinge region-binding fragments.
2013
Protein kinases constitute an attractive family of enzyme targets with high relevance to cell and disease biology. Small molecule inhibitors are powerful tools to dissect and elucidate the function of kinases in chemical biology research and to serve as potential starting points for drug discovery. However, the discovery and development of novel inhibitors remains challenging. Here, we describe a structure-based de novo design approach that generates novel, hinge-binding fragments that are synthetically feasible and can be elaborated to small molecule libraries. Starting from commercially available compounds, core fragments were extracted, filtered for pharmacophoric properties compatible w…