72035-56-4Relevant academic research and scientific papers
One-pot synthesis of 3-substituted-3-hydroxyindolin-2-ones: three component coupling ofN-protected isatin, aryne precursor and 1,3-cyclodione under metal-free conditions
Chutia, Kangkana,Das, Babulal,Gogoi, Pranjal,Hazarika, Hemanta
, p. 86 - 96 (2021/12/31)
An aryne-based synthetic protocol has been developed for the synthesis of 3-substituted-3-hydroxy-indolin-2-ones. A wide variety of 3-hydroxyindolin-2-ones were synthesized in good yields under metal-free conditionsviathree component coupling ofN-protected isatin, aryne precursor, and 1,3-cyclodione. One of our synthesized compounds has been unambiguously confirmed by single crystal XRD analysis. Further, treating the synthesized 3-hydroxyindolin-2-one derivatives with an inorganic base at high temperature leads to an interestingo-arylated product of 1,3-cyclohexandione.
Support-Free Pd3Co NCs as an Efficient Heterogeneous Nanocatalyst for New Organic Transformations of C?C Coupling Reactions
Pradhan, Samjhana,Mishra, Kanchan,Lee, Yong Rok
, p. 10886 - 10894 (2019/08/02)
A support-free heterogeneous Pd3Co nanostructured composite (NC), synthesized through a hydrothermal route, acted as an effective catalytic system in multivariate Heck-, Sonogashira-, and Suzuki-type coupling reactions of iodonium ylides. The XPS analysis of the bimetallic Pd3Co NCs confirmed the elemental composition as 75 % palladium and 25 % cobalt. Furthermore, high-resolution (HR) TEM analysis confirmed the spherical morphology of the Pd3Co bimetallic nanoparticles. The average diameter of the NCs is 14.8 nm. The coupling reaction proceeded through the generation of α-iodoenones with simultaneous migration of the phenyl group, thereby giving a scaffold with higher atom economy. The heterogeneous Pd3Co NCs were recycled and reused without any significant change in catalytic ability for up to five reaction cycles. The high concentration of Pd and association of cobalt into the lattice of palladium appears to enhance its catalytic ability for the diverse coupling reactions in comparison with its monometallic counterparts as well as with bimetallic NCs with a comparatively lesser amount of Pd.
Copper-catalyzed regio- and stereoselective O-arylation of enolates
Xu, Ze-Feng,Cai, Chen-Xin,Jiang, Min,Liu, Jin-Tao
supporting information, p. 3436 - 3439 (2014/07/21)
Copper-catalyzed O-arylation of enolates with diaryliodonium salts as arylating reagents was realized successfully. As important building blocks, β-aryloxy carbonyl compounds were obtained in up to 98% yield under mild conditions, and complete control of
COPPER CATALYSED O-PHENYLATION OF PHENOLS AND ENOLS BY PENTAVALENT ORGANOBISMUTH COMPOUNDS
Barton, Derek H. R.,Finet, Jean-Pierre,Khamsi, Jamal,Pichon, Clotilde
, p. 3619 - 3622 (2007/10/02)
The O-phenylation of phenols under neutral conditions by Bi(V) reagents is strongly catalysed by copper salts and by copper powder, even at room temperature.Enolic systems are also subject to copper powder catalysis and give exclusively O-phenylation.
Reduction of Vinylogous Thioesters with Lithium Aluminum Hydride. I. Reduction of β-Phenylthio-α,β-unsaturated Cyclic Ketones
Matoba, Katsuhide,Tokizawa, Minoru,Morita, Takashi,Yamazaki, Takao
, p. 368 - 372 (2007/10/02)
5,5,Dimethyl-3-phenoxy-2-cyclohexenone (Ib) was reduced with lithium aluminum hydride (LAH) to give the 1,2-addition product (IIIa). 2-Methyl-3-phenoxy-2-cyclopentetnone (IIa) gave a mixture of the allyl alcohol (IVa) and 1,2-addition product (IVb).On the
Pentavalent Organobismuth Reagents. Part 3. Phenylation of Enols and of Enolate and other Anions
Barton, Derek H. R.,Blazejewski, Jean-Claude,Charpiot, Brigitte,Finet, Jean-Pierre,Motherwell, William B.,et al.
, p. 2667 - 2676 (2007/10/02)
The phenylation of enols and of enolate anions of ketones, β-diketones and keto esters has been studied using a range of Bi reagents.Under basic conditions C-phenylation is observed and, even hindered, perphenylated compounds are easily synthesized.Under neutral and acidic conditions ordinary ketones do not react and enolic systems give O-phenylation.A number of other anions have been phenylated under basic conditions, including the key compound indole wich mainly gave 3-C-phenylation.All these reactions can be supposed to have one of two alternative mechanisms, which parallel the two mechanisms proposed for the phenylation of phenols.
REACTION OF CYCLIC SELENIUM DIKETOYLIDES WITH DIPHENYLCYCLOPROPENONE
Magdesieva, N. N.,Gordeev, M. F.,Kyandzhetsian, R. A.
, p. 2129 - 2134 (2007/10/02)
In reaction with diphenylcyclopropenone dimethylselenonioindanedionide only forms 5-oxo-3,4-diphenylindeno-2-pyrone.The reaction of diphenylcyclopropenone with dimethylselenoniodimedolide leads to the formation of condensed α- and γ-pyrones and also the product from addition of the ketocarbene of dimedone at the double bond of cyclopropenone and dimedone α-phenylcinnamate.The sulfonionindanedionide forms the 2-indenopyrone appreciably more slowly than the selenonium analog and with half the yield.Condensed pyrones are not formed at all in the reaction of the sulfoniodimedonide.
REGIOSPECIFIC ARYLATION BY ACID/BASE CONTROLLED REACTIONS OF TETRAPHENYLBISMUTH ESTERS
Barton, Derek H. R.,Charpiot, Brigitte,Motherwell, William B.
, p. 3365 - 3368 (2007/10/02)
Tetraphenylbismuth V reagents react with enolic systems under acidic or basic conditions to give predictably different intermediates; these fragment with variable, but anticipated, regioselectivity.
Arynic Condensations of Ketone Enolates. 15. New Synthetic Applications of the Condensation of α,β-Unsaturated Ketone Enolates on Benzyne
Essiz, Munir,Guillaumet, Gerald,Brunet, Jean-Jacques,Caubere, Paul
, p. 240 - 246 (2007/10/02)
Arynic condensations of both cyclic and acyclic α,β-unsaturated ketone enolates are studied.First, condensation of substituted cyclohexenone enolates with benzyne leads to a new class of cyclobutanic alcohols 6.Ring opening of 6 under basic conditions is described as a good means of synthesizing benzocyclooctadienones 10 and 19, and, in appropriate cases, benzocyclooctenediones of type 12.Thermal dehydration of 6 affords 1,3-disubstituted naphthalenes in good yields.Second, condensations of a few acyclic α,β-unsaturated ketone enolates with benzyne are shown to be of synthetic usefulness; depending on the substituents on both sides of the carbonyl group, these condensations may lead either to substituted naphthalenes or to phenyl ketones or tetralones.
