69202-72-8Relevant academic research and scientific papers
A simple iron-catalyst for alkenylation of ketones using primary alcohols
Sk, Motahar,Kumar, Ashish,Das, Jagadish,Banerjee, Debasis
, (2020/04/10)
Herein, we developed a simple iron-catalyzed system for the α-alkenylation of ketones using primary alcohols. Such acceptor-less dehydrogenative coupling (ADC) of alcohols resulted in the synthesis of a series of important α,β-unsaturated functionalized ketones, having aryl, heteroaryl, alkyl, nitro, nitrile and trifluoro-methyl, as well as halogen moieties, with excellent yields and selectivity. Initial mechanistic studies, including deuterium labeling experiments, determination of rate and order of the reaction, and quantitative determination of H2 gas, were performed. The overall transformations produce water and dihydrogen as byproducts.
Regioselective synthesis of dispirocycloalkanooxindolopyrrolidines and dispirocyclalkanoindanopyrrolidines
Poornachandran, Mahalingam,Jayagobi, Mathesan,Raghunathan, Raghavachary
body text, p. 551 - 563 (2010/04/06)
Synthesis of a series of novel dispirocycloalkanone-oxindolopyrrolidines and dispirocycloalkanone-indanopyrrolidines is described. The nonstabilized azomethine ylides generated from a secondary amino acid, sarcosine, and carbonyl components (isatin and ninhydrin) have been effectively trapped by the dipolarophiles, arylidene cycloalkanones, to afford dispiropyrrolidines. The one-pot azomethine ylide cycloaddition reactions were highly regioselective. Copyright Taylor & Francis Group, LLC.
Claisen-schmidt condensation catalyzed by metal-organic frameworks
Dhakshinamoorthy, Amarajothi,Alvaro, Mercedes,Garcia, Hermenegildo
experimental part, p. 711 - 717 (2010/06/13)
Metal-organic framework [Fe(BTC) (BTC = 1,3,5-benzenetricarboxylic acid)] is a convenient heterogeneous catalyst for the carbon-carbon bond forming reaction in toluene between acetophenone and benzaldehyde to give selectively chalcone in high yield. Fe(BTC) appears as a general catalyst able to synthesize selectively different chalcone derivatives bearing various functionalities. Fe(BTC) could be recycled with no significant loss of catalytic efficiency and crystallinity in subsequent runs.
Regioselective synthesis of rac-(1R,4R,6R,6aR)-6′-phenyl-7′, 8′-dihydro-1″H,2′H,6′H-dispiro[cycloalkane-1, 5′-pyrrolo[1,2-c][1,3]thiazole-4′,3″-indole]-2, 2″-diones through 3 + 2 cycloaddition reaction
Poornachandran, Mahalingam,Jayagobi, Mathesan,Raghunathan, Raghavachary
scheme or table, p. 240 - 243 (2009/12/07)
Synthesis of a series of novel rac-(1R,4R,6R,6aR)-6′-phenyl-7′, 8′-dihydro-1″H,2′H,6′H-dispiro[cycloalkane-1, 5′-pyrrolo[1,2-c][1,3]thiazole-4′,3″-indole]-2, 2″-diones by cycloaddition reaction is described. The nonstabilised azomethine ylide generated by the reaction of isatin and thiazolidine-2- carboxylic acid has been regioselectively trapped by various substituted benzylidene cycloalkanones.
Highly enantioselective synthesis of optically active ketones by iridium-catalyzed asymmetric hydrogenation
Lu, Sheng-Mei,Bolm, Carsten
supporting information; experimental part, p. 8920 - 8923 (2009/05/30)
(Chemical Equation Presented) Close to perfect enantioselectivity (up to 99% ee, see scheme) is found for the formation of α-substituted ketones by the asymmetric hydrogenation of enones with an iridium-phosphinooxazoline catalyst. In an operationally simple process, both linear and cyclic substrates react well and afford the desired products in high yields. A wide variety of substituents are tolerated, thus making the method synthetically appealing.
A new lewis acid system palladium/TMSCl for Catalytic aldol condensation of aldehydes with ketones
Zhu, Yulin,Pan, Yuanjiang
, p. 668 - 669 (2007/10/03)
Palladium on charcoal effectively catalyzed the aldol condensation reactions of different ketones with aldehydes in the presence of trimethylsilyl chloride (TMSCl). The following reactions were investigated: (1) aromatic aldehydes with cycloalkanones, (2) aromatic aldehydes with aromatic ketones, (3) cycloalkanones with aliphatic aldehydes, and (4) the self-condensation reactions of aliphatic aldehydes and cycloalkanones.
Expedient synthesis of unsaturated amide alkaloids from Piper spp: Exploring the scope of recent methodology
Strunz, George M.,Finlay, Heather J.
, p. 419 - 432 (2007/10/03)
The Sakai aryl aldehyde - cyclic ketone aldol - Grob fragmentation sequence was extended to cinnamaldehyde and cyclohexanone, and the product was elaborated to analogues of the alkaloid piperstachine. The effects of substituents on the reaction involving cinnamaldehyde were studied. The aldol-fragmentation sequence failed with benzaldehyde when cyclooctanone or cyclobutanone was substituted for cyclohexanone or cyclopentanone, and the reasons for this failure were examined. Four-carbon Wittig homologation of the piperonal-cyclobutanone aldol-fragmentation product, a hypothetical route to alkaloids such as retrofractamide A, was thus not viable. Instead, three-carbon homologation of the readily available piperonal-cyclopentanone product, using alkyne chemistry recently disclosed by Lu and Trost, afforded these alkaloids in excellent overall yield. The alkyne isomerization was also used to effect efficient syntheses of pellitorine and several other non-aromatic 2E,4E-dienoic Piper amide alkaloids. The Sakai aryl aldehyde - cyclic ketone aldol - Grob fragmentation sequence was extended to cinnamaldehyde and cyclohexanone, and the product was elaborated to analogues of the alkaloid piperstachine. The effects of substitutents on the reaction involving cinnamaldehyde were studied. The aldol-fragmentation sequence failed with benzaldehyde when cyclooctanone or cyclobutanone was substituted for cyclohexanone or cyclopentanone, and the reasons for this failure were examined. Four-carbon Wittig homologation of the piperonal-cyclobutanone aldol-fragmentation product, a hypothetical route to alkaloids such as retrofractamide A, was thus not viable. Instead, three-carbon homologation of the readily available piperonal-cyclopentanone product, using alkyne chemistry recently disclosed by Lu and Trost, afforded these alkaloids in excellent overall yield. The alkyne isomerization was also used to effect efficient syntheses of pellitorine and several other non-aromatic 2E,4E-dienoic Piper amide alkaloids.
Ring-opening of isoxazolidine nucleus: Competitive formation of α,β-enones and tetrahydro-1,3-oxazines
Casuscelli, Franco,Chiacchio, Ugo,Rescifina, Antonio,Romeo, Roberto,Romeo, Giovanni,Tommasini, Silvana,Uccella, Nicola
, p. 2979 - 2990 (2007/10/02)
Treatment of isoxazolidine derivatives with methyl iodide, followed by simple heating with aqueous NaOH, gives rise to a competitive formation of α,β-enones and tetrahydro-1,3-oxazines. The ring-opening process is controlled by the stereochemistry of H5 which represents the driving factor of two competitive reaction routes.
N,O-HETEROCYCLES. XVI. DIRECT CONVERSION OF SOME ISOXAZOLIDINES INTO ALCOHOLS VIA α,β-ENONES
Liguori, Angelo,Sindona, Giovanni,Uccella, Nicola
, p. 369 - 374 (2007/10/02)
The 1,3-dipolar cycloadducts between nitrones and alkenes are converted into alcoholic derivatives by trimethyl phosphate and by subsequent reduction.The reaction of the substituted isoxazolidines, exempt of further functionalities, proceeds under the action of TMP through a sequence of steps including a Hofmann-like elimination with electronic-controlled orientation indicated also by thermochemical calculations.The overall process leads to the formation of saturated and unsaturated alcohols as known for the reduction step.
