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Search for "baclofen" in Full Text gives 8 result(s) in Beilstein Journal of Organic Chemistry.
Enantioselective synthesis of β-aryl-γ-lactam derivatives via Heck–Matsuda desymmetrization of N-protected 2,5-dihydro-1H-pyrroles
Beilstein J. Org. Chem. 2024, 20, 940–949, doi:10.3762/bjoc.20.84
- commercial drug baclofen as hydrochloride. Keywords: desymmetrization; enantioselective Heck–Matsuda reaction; lactam synthesis; N,N-ligands; palladium; Introduction Desymmetrization reactions consist in the modification of a molecule with the loss of one or more symmetry elements, such as those which
- inhibitor (R)-rolipram (5b) [15], and the commercial drug (R)-baclofen hydrochloride (6), used to treat muscle spasticity from spinal cord injury and multiple sclerosis [16]. Results and Discussion Desymmetrization of N-protected 2,5-dihydro-1H-pyrroles Some initial results and reaction optimization Based
- Supporting Information File 1 for details). Given the presence of the 4-aryl-γ-lactam motif in the phosphodiesterase-4 inhibitor rolipram, and in a synthetic intermediate for the baclofen drug, the Heck products 4bg and 4bq were used as starting material for their syntheses. N-Tosylated lactams 4bg and 4bq
Palladium-catalyzed three-component radical-polar crossover carboamination of 1,3-dienes or allenes with diazo esters and amines
Beilstein J. Org. Chem. 2024, 20, 661–671, doi:10.3762/bjoc.20.59
- owing to their wide applications in medicinal chemistry [1][2][3][4][5]. γ- and ε-AA derivatives are widely distributed in peptide natural products, bioactive molecules, and drugs, such as pregabalin, baclofen, ε-aminocaproic acid and lysine (Scheme 1a) [6][7][8][9][10][11][12]. The number of reported
A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen
Beilstein J. Org. Chem. 2023, 19, 1811–1824, doi:10.3762/bjoc.19.133
- % ee). Moreover, 1 mol % of the catalyst was feasible to conduct the gram-scale preparation of baclofen precursor (89% yield, 96% ee). Finally, thanks to the lipophilic character of the catalyst, it was easily recycled after the reaction by replacing the non-polar reaction solvent with a polar solvent
- , acetonitrile, with 91–100% efficiency, and the catalyst was reused in five reaction cycles without the loss of activity and selectivity. Keywords: baclofen; catalyst recovery; lipophilic cinchona squaramide; organocatalysis; stereoselective catalysis; Introduction In today’s chemical industry, catalytic
- cinchona squaramide organocatalyst. Its catalytic activity and recyclability were examined in a new stereoselective synthesis of baclofen, which is used to treat muscle spasms [30]. Finally, the catalyst was easily recycled by centrifugation over five reaction cycles without significant loss of activity
Investigations towards the stereoselective organocatalyzed Michael addition of dimethyl malonate to a racemic nitroalkene: possible route to the 4-methylpregabalin core structure
Beilstein J. Org. Chem. 2018, 14, 553–559, doi:10.3762/bjoc.14.42
- . Stereoselective Michael addition, one of the most important organocatalytic reactions [8] usually serves as a key stereoinduction transformation. Earlier studies, performed by Hayashi and Wang employed iminium activation to perform the enantioselective addition of nitromethane to enals for syntheses of baclofen
Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides
Beilstein J. Org. Chem. 2018, 14, 309–317, doi:10.3762/bjoc.14.19
- pharmaceuticals, such as γ-aminobutyric acid (GABA) and γ-amino-β-hydroxybutyric acid (GABOB) analogues (baclofen HCl and pregabalin) [51][52][53][54], HMG-CoA reductase inhibitors (“statins”) [55][56][57], etc. The generality and scope of this methodology was further demonstrated in the alcoholysis of 8a with
Continuous-flow synthesis of primary amines: Metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane
Beilstein J. Org. Chem. 2016, 12, 2614–2619, doi:10.3762/bjoc.12.257
- synthetically relevant intermediates (precursors of baclofen and boscalid). Keywords: chemoselectivity; continuous processes; flow synthesis; nitro reduction; trichlorosilane; Introduction The reduction of nitro compounds to amines is a fundamental transformation in organic synthesis. The nitration of
- [29]. The corresponding amide 6 is a direct precursor of the GABA receptor agonist Baclofen (Scheme 5). Nitro compound 5 was continuously reduced in a 5 mL reactor and, after work-up under neutral conditions, chiral lactam 6 was isolated in 48% yield. Finally we explored the possibility of performing
- )aniline (4) with a 5 mL flow reactor. Synthesis of intermediate 6, a direct precursor of the drug baclofen. Continuous-flow reduction of 1a and in-line extraction. Screening of reaction conditions. Scope of the reaction (see Scheme 2). Supporting Information Supporting Information File 488: General
Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams
Beilstein J. Org. Chem. 2015, 11, 530–562, doi:10.3762/bjoc.11.60
- enantioselectivities than phosphine ligands in rhodium-catalyzed asymmetric reactions [152][153]. Scheme 16 shows the rhodium-catalyzed asymmetric 1,4-arylation that was developed by Lin and co-workers and the subsequent transformation to the GABAB receptor agonist, (R)-(−)-baclofen. Much of the work that has been
Synthesis of the calcilytic ligand NPS 2143
Beilstein J. Org. Chem. 2013, 9, 1383–1387, doi:10.3762/bjoc.9.154
- -aminobutyric acid type B (GABAB) receptors, three taste (TR) receptors, the GPRC6A receptor, the calcium-sensing receptor (CaSR), and seven orphan receptors [4]. Class C GPCRs have proven viable as drug targets, exemplified by the marketed GABAB agonist baclofen, and by cinacalcet (1), a positive allosteric
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