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Search for "oxindoles" in Full Text gives 82 result(s) in Beilstein Journal of Organic Chemistry.
Direct alkenylation of indolin-2-ones by 6-aryl-4-methylthio-2H-pyran-2-one-3-carbonitriles: a novel approach
Beilstein J. Org. Chem. 2013, 9, 809–817, doi:10.3762/bjoc.9.92
- hydride-AIBN initiated radical cyclization [33][34]. In 2005, Player and co-workers reported a tandem Heck/Suzuki–Miyaura coupling process for the synthesis of (E)-3,3-(diaryl)oxindoles [35][36][37]. Recently, alkenylation of indolin-2-ones has been developed by palladium-catalyzed aromatic C–H activation
- 3-alkenyl-2-oxindoles being based on expensive catalysts, non-commercially available precursors, and multistep time-consuming synthetic protocols, the development of an efficient, economical and short synthesis was inevitable and desirable. In this regard, we have now developed an efficient new
- protocol for the direct alkenylation of 2-oxindole by 6-aryl-4-methylthio-2H-pyran-2-one-3-carbonitriles 3 to deliver 3-alkenyl-2-oxindoles 8 in moderate yield. This procedure is quite efficient, noncatalytic, economical and easy in workup. Moreover, it opens a new avenue for the synthesis of 3-alkenyl-2
Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione
Beilstein J. Org. Chem. 2013, 9, 8–14, doi:10.3762/bjoc.9.2
- [3][4][5][6]. Isatin and its derivatives may be the most useful starting materials or precursors in the synthesis of a wide number of spirocyclic oxindoles [7][8]. Due to its simple process, easy operation, efficiency and high atomic economy, the multicomponent reaction based on isatin and its
- ][13][14]. Considering the above reports, and as part of our program aimed at developing new multicomponent reactions for the construction of complex heterocyclic compounds, we wish in this work to report the efficient synthesis of unprecedented cyclopentyl-fused spiro[dihydropyridine-oxindoles] by the
- condensation of isatins with cyclic 1,3-dicarbonyl compounds [30][31][32][33], the condensation reaction of isatin with cyclopentane-1,3-dione seemed still not to have been investigated and the 3,3-bis(2-hydroxy-5-oxo-cyclopent-1-enyl)oxindoles 3a–3d have not been prepared until now. Thus, the direct
Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone
Beilstein J. Org. Chem. 2012, 8, 1360–1365, doi:10.3762/bjoc.8.157
- Michael addition of unprotected 3-prochiral oxindoles 1 to 1,4-naphthoquinone. Quinidine derivative (DHQD)2PYR was found to be able to catalyze this reaction in up to 83% ee, with moderate to excellent yields. This method could be used for the synthesis of enantioenriched 3,3-diaryloxindoles, and the
- catalytic synthesis of which was unprecedented. Keywords: 3,3-disubstituted oxindoles; Michael addition; organocatalysis; quaternary stereogenic center; unprotected 3-substituted oxindoles; Introduction The catalytic asymmetric synthesis of 3,3-disubstituted oxindoles has recently received great attention
- biological activities [4]. Accordingly, the development of efficient synthetic methods to enable the synthesis of 3,3-disubstituted oxindoles in great structural diversity is of current interest, and much progress had been made in the catalytic enantioselective synthesis of 3-hydroxyoxindoles [5][6][7][8][9
Organocatalytic asymmetric allylic amination of Morita–Baylis–Hillman carbonates of isatins
Beilstein J. Org. Chem. 2012, 8, 1241–1245, doi:10.3762/bjoc.8.139
- investigation of a Lewis base catalyzed asymmetric allylic amination of Morita–Baylis–Hillman carbonates derived from isatins afforded an electrophilic pathway to access multifunctional oxindoles bearing a C3-quaternary stereocenter, provided with good to excellent enantioselectivity (up to 94% ee) and in high
- yields (up to 97%). Keywords: allylic amination; asymmetric organocatalysis; Morita–Baylis–Hillman carbonates; 2-oxindoles; quaternary chiral center; Introduction Chiral 3-amino-2-oxindoles are versatile and useful units for the preparation of natural products and drug candidates, such as the
- oxindoles as nucleophiles in the reactions with azodicarboxylates or nitrosobenzene provides a very simple and direct approach for the synthesis of optically active 3-amino-2-oxindole derivatives [7], either by the catalysis of chiral metal complexes [8][9][10] or organic catalysts [11][12][13][14][15]. On
Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles
Beilstein J. Org. Chem. 2011, 7, 601–605, doi:10.3762/bjoc.7.70
- oxindoles into chiral non-racemic spirooxindoles containing an alkylidene cyclobutene moiety. The enantiomeric excesses were determined by chiral lanthanide shift NMR analysis and the transfer of chiral information from the allene to the spirooxindole was found to be greater than 95%. Keywords: alkylidene
Total synthesis of (±)-coerulescine and (±)-horsfiline
Beilstein J. Org. Chem. 2010, 6, 876–879, doi:10.3762/bjoc.6.103
- 60% yield. The physical data of synthetic coerulescine and horsfiline were comparable in all respects with the literature data. Conclusion In summary, we have described a new and efficient synthesis of (±)-coerulescine and (±)-horsfiline. Spiro[pyrrolidin-3,3'-oxindoles]. Reagents and conditions: a
DBFOX- Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones
Beilstein J. Org. Chem. 2008, 4, No. 16, doi:10.3762/bjoc.4.16
- fluorination of a wide range of substrates, including β-keto esters, β-keto phosphonates, oxindoles [38][40][43][51][53][56][57]. They have also recently reported the enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones with their extended catalytic system, NiCl2-BINAP/R3SiOTf-lutidine with high
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