Syntheses of Substituted Indan 1 ones and Indenes

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Synthesis of Substituted 4‐Aroyl‐1‐indanone and 5‐Aroyl‐1‐tetralone

Several substituted 4‐aroyl‐1‐indanones 2 and 5‐aroyl‐1‐tetralones 3 were prepared in good yields from 1‐indanones 1 via a series of reasonable transformations.     

Rhodium-catalyzed isomerization of alpha-arylpropargyl alcohols to indanones: involvement of an unexpected reaction cascade

A rhodium-catalyzed isomerization of alpha-arylpropargyl alcohols to indanones has been developed under mild conditions. Considering the ease of preparation of these propargyl alcohols (terminal alkynes + aromatic aldehydes), this method provides a new way of constructing indanones with high efficiency. By the mechanistic investigations using deuterium-labeled substrates, it has also been demonstrated that the reaction goes through an unexpected cascade, with a 1,4-hydrogen shift being the turnover-limiting step of the catalytic cycle.     

Transition metal catalyzed carboannulation of diazabicyclic alkenes with ambiphilic bifunctional reagents: a facile route towards functionalized indanones and indanols

Functionalized indanones are readily prepared in good to excellent yields by the Pd/Rh catalyzed carboannulation of bicyclic and tricyclic hydrazines with 2-iodobenzonitrile, 2-cyanophenylboronic acid and 2-formylphenylboronic acid. The reaction with 2-formylphenylboronic acid afforded 3,4-disubstituted cyclopentenes as minor product along with indanones under Rh catalyzed conditions, whereas indanols were obtained as the major product under Pd catalyzed conditions. The products obtained can be synthetically manipulated easily to pharmaceutically important molecules.     

Application of the intramolecular isomerisation-aldolisation from allylic alcohols and allylic silyl ethers to the synthesis of indanones and indenones

A new access to indanones was discovered through a one-step nickel or iron-mediated transposition of 2-hydroxyisobenzofurans. Starting from the corresponding silylenol ethers, a new one-pot tandem isomerisation-Mukaiyama aldol process was also developed. These versatile strategies will be useful for the preparation of various types of indanones and indenones.     

A Systematic Investigation of Long-Range Couplings in the 1H NMR Spectra of Dimeric Indanones

 During the synthesis of methyl substituted indanones by intramolecular cyclization of 3-phenyl-propionic acids, dimerization led to by-products which can be considered as dimeric indanones. The proton NMR spectra of these compounds exhibit pronounced scalar couplings over up to seven bonds. A series of structures of the above type were investigated, and their NMR spectroscopic behaviour is discussed.     

A Facile Synthesis of Novel Dihydroindeno[1,2‐e][1,2,4]triazolo[3,4‐b][1,3,4]thiadiazines Using HTIB

The synthesis of a series of 21 novel 3‐alkyl/aryl‐7/9‐methyl‐10,10a‐dihydroindeno[1,2‐e][1,2,4]triazolo[3,4‐b][1,3,4]thiadiazines ( 4 ) has been achieved by the cyclocondensation between 4/6‐methyl‐2‐tosyloxy‐1‐indanones ( 2 ) and 3‐alkyl/aryl‐4‐amino‐5‐mercapto‐1,2,4‐s‐triazoles ( 3 ). 4/6‐Methyl‐2‐tosyloxy‐1‐indanones ( 2 ) were readily accessible through hypervalent iodine oxidation of 4/6‐methyl‐1‐indanones using [(hydroxy)tosyloxyiodo]benzene (HTIB, Koser's reagent) in acetonitrile.     

Arynic condensation of ketone enolates—XIV: Condensation of aromatic α,β-unsaturated ketone enolates on arynes

Benzyne and 1-naphthyne (generated from the corresponding halogeno derivatives and the Complex Base NaNH₂-Bu^tONa) condense with α,β-unsaturated ketone enolates β-substituted by an aromatic ring and only enolisable in the α'-position, to lead to α-tetralones and/or indanones. The reaction path depends upon the nature of the ketone enolate and, less strongly, on the solvent. The reaction mechanism is discussed. These reactions constitute new simple and efficient syntheses of numerous α-tetralones and indanones.     

Convenient Synthetic Sequence for the Preparation of Indanones

A convenient and general method is reported for the synthesis of indanones from aryl ketones or aldehydes.     

Pd‐Catalyzed Enantioselective Ring Opening/Cross‐Coupling and Cyclopropanation of Cyclobutanones

A palladium‐catalyzed enantioselective sequential ring‐opening/cross‐coupling of cyclobutanones is disclosed that provides chiral indanones bearing C3‐quaternary stereocenters. The reaction process involves palladium‐catalyzed nucleophilic addition of cyclobutanones and aryl halides, enantioselective β‐carbon elimination, and intermolecular trapping of a transient σ‐alkylpalladium complex with boronic acids. Alternatively, an intramolecular cyclopropanation is realized through C?H bond functionalization in the absence of external coupling reagents, affording chiral cyclopropane‐fused‐indanones in good yields and enantioselectivity.     

1,2,3,4-tetrasubstituted isoquinoline acetic acids

Differentially tetrasubstituted isoquinolines are now conveniently prepared by rearrangement of the readily obtainable indanones.     

Preparation of Acrylophenones and 2-Alkyl Indanones Utilizing Hexamethylenetetramine as an Inexpensive Mannich Reagent.

Hexamethylenetetramine/acetic anhydride-promoted α-methylenation of aryl alkyl ketones followed by acid-catalyzed cyclization of the resulting acrylophenones produce 2-alkyl indanones in excellent yields.     

Novel one-pot approach to synthesis of indanones through Sb(V)-catalyzed reaction of phenylalkynes with aldehydes

Catalytic SbF5 and the use of EtOH as an additive efficiently converted a mixture of phenylalkynes and aldehydes to indanone compounds in one pot, and the reaction stereoselectively afforded the corresponding 2,3-disubstituted indanones as a single trans-isomer.     

The synthesis of indanones related to combretastatin A-4 via microwave-assisted Nazarov cyclization of chalcones

A fast and efficient microwave-assisted synthesis of combretastatin A-4-like indanones has been developed. Microwave irradiation provides a useful alternative to traditional heating techniques to promote the TFA-catalyzed Nazarov cyclization of chalcones.     

A convenient two step protocol for the synthesis of cyclopentenones and indanones,including an asymmetric variant

A one-pot palladium mediated hydrostannylation/cross-coupling protocol is used to give direct access to cross-conjugated dienones that can be utilized in Nazarov cyclizations to afford highly substituted cyclopentenones and indanones, including an asymmetric variant.     

Solvent-dependent behavior of arylvinylketones in HUSY-zeolite: a green alternative to liquid superacid medium

Depending on the reaction conditions, arylvinylketones can be directly and efficiently converted using zeolites to indanones by cyclization or to dihydrochalcones through regioselective aryl addition or chemoselective hydride transfer.     

Synthesis of fused 4,5-disubstituted indole ring systems by intramolecular friedel-crafts acylation of 4-substituted indoles

4-Substituted indoles containing a variety of electrophiles and N-substituents undergo Friedel-Crafts acylation to give exclusively the products of cyclization at the 5-position of indole. These indanones and tetralones have been scarcely prepared and are subunits in natural products and analogues of potential biological significance.     

Rhodium-catalyzed addition of arylzinc reagents to aryl alkynyl ketones: synthesis of beta,beta-disubstituted indanones

A rhodium-catalyzed addition of arylzinc reagents to aryl alkynyl ketones for the synthesis of highly substituted indanones has been developed. The key to success has proved to be a proper choice of the reaction system, which involves the employment of dppf as a ligand and 1,2-dichloroethane as a solvent.     

Synthesis of indanones via solid-supported [2+2+2] cyclotrimerization

A new facile approach toward natural and unnatural indanones has been developed, featuring a solid-supported [2+2+2] cyclotrimerization as the key step. This strategy has been applied to the chemo- and regioselective assembly of indanone arrays and to the total synthesis of a recently isolated indanone marine natural product.     

一种光化学合成取代茚酮的有效方法

介绍了一种利用光诱导分子内氢转移形成烯醇化反应进而有效合成取代茚酮的光化学方法.所合成的酯具有较高的光化学反应活性,光反应的产率高,产物易分离纯化.