Indene Derivatives Research Articles

ChemInform Abstract: Highly Selective Introduction of Heteroatom Groups to Isocyanides and Its Application to Electrocyclic Reactions

AbstractReview: 34 refs.

Synthesis of Diverse Indene Derivatives from 1-Diazonaphthalen-2(1H)-ones via Thermal Cascade Reactions

A sequential Wolff rearrangement of 1-diazonaphthalen-2(1H)-ones followed by trapping of the ketene intermediate with primary and aromatic amines or alcohols and phenols in the presence of various aldehydes generates 1H-indene-3-carboxamides or 1H-indene-3-carboxylates. This constitutes an unprecedented three-component coupling reaction that allows for the synthesis of functionalized indene derivatives under catalyst-free thermal conditions.

ChemInform Abstract: Synthesis of Indene Frameworks via Rhodium‐Catalyzed Cascade Cyclization of Aromatic Ketone and Unsaturated Carbonyl Compounds.

AbstractA novel Rh(III)‐catalyzed direct functionalization of the ortho‐C—H bond of aromatic ketones followed by an intramolecular cyclization gives indene derivatives in moderate to good yields.

Palladium‐Catalyzed Route to Three‐Component, One‐Pot Sequential Synthesis of Functionalized Cyclazines: 2,2a1,4‐Triazacyclopenta[cd]indenes

AbstractAn efficient tandem route to the synthesis of 2,2a1,4‐triazacyclopenta[cd]indene derivatives of the cyclazine family has been developed. The target compounds were obtained in moderate to good yields by an ytterbium(III) triflate/palladium(II) acetate‐catalyzed three‐component domino reaction involving a palladium‐catalyzed intramolecular α‐arylation of an α‐aminocarbonyl functionality. This in turn will set the stage for a wide application of this useful reaction for the synthesis of structurally diverse polyheterocyclic skeletons containing the privileged imidazo[1,2‐a]pyridine structure.

FeCl3-Mediated Cyclization of [60]Fullerene with N-Benzhydryl Sulfonamides under High-Speed Vibration Milling Conditions

The FeCl3-mediated reaction of [60]fullerene with N-benzhydryl sulfonamides afforded C60-fused indane derivatives using the high-speed vibration milling technique. A possible reaction mechanism involving the unprecedented FeCl3-mediated homolytic C-N bond cleavage of N-benzhydryl sulfonamides is proposed. The electrochemistry of the obtained C60-fused indanes was also investigated.

ChemInform Abstract: One‐Pot Synthesis of Indene Derivatives by CF3SO3H‐Promoted Reactions of Benzylic Alcohols and 1,3‐Dicarbonyl Compounds.

AbstractThe coupling/cyclization sequence produces indene structures of type (III) as main or exclusive regioisomers.

Iridium(III)‐Catalyzed Approach for the Synthesis of Fused Arenes: Access to Isoindolines, Indanes, and Dihydroisobenzofurans

AbstractA facile and efficient method for the synthesis of isoindoline, indane, and dihydroisobenzofuran derivatives has been developed through the application of a halogen‐bridged iridium(III) complex to the [2+2+2] cycloaddition of α,ω‐diynes with alkynes. The cycloaddition tolerates a broad range of substitution groups, such as alcohol, alkyl, ether, and halogen, and the chemistry can be extended to prepare the corresponding borylated fused arenes. The reaction shows that hindered starting materials are also good partners, which provide the desired fused arenes in good yields.

Polarity and Air-Stability Transitions in Field-Effect Transistors Based on Fullerenes with Different Solubilizing Groups

A series of o-xylene and indene fullerene derivatives with varying frontier molecular orbital energy levels were utilized for assessing the impact of the number of solubilizing groups on the electrical performance of fullerene-based organic-field-effect transistors (OFETs). The charge-carrier polarity was found to be strongly dependent upon the energy levels of fullerene derivatives. The o-xylene C60 monoadduct (OXCMA) and indene C60 monoadduct (ICMA) exhibited unipolar n-channel behaviors with high electron mobilities, whereas the bis- and trisadducts of indene and o-xylene C60 derivatives showed ambipolar charge transport. The OXCMA OFETs fabricated by solution shearing and molecular n-type doping showed an electron mobility of up to 2.28 cm(2) V(-1) s(-1), which is one of the highest electron mobilities obtained from solution-processed fullerene thin-film devices. Our findings systematically demonstrate the relationship between the energy level and charge-carrier polarity and provide insight into molecular design and processing strategies toward high-performance fullerene-based OFETs.

ChemInform Abstract: FeCl3 Catalyzed Prins‐Type Cyclization for the Synthesis of Highly Substituted Indenes: Application to the Total Synthesis of (.+‐.)‐Jungianol and epi‐Jungianol.

A novel approach was developed for the synthesis of highly substituted indene derivatives, using an FeCl(3) catalyzed Prins-type cyclization reaction which was further applied in the total synthesis of jungianol and epi-jungianol.

1,2,3,4‐Tetrasubstituted Cyclopentadienes and Their Applications for Metallocenes: Efficient Synthesis through Zirconocene‐ and CuCl‐Mediated Intermolecular Coupling of Two Alkynes and One Diiodomethane

1,2,3,4-Tetrasubstituted cyclopentadienes and indene derivatives with identical or different substituents were obtained in good to excellent isolated yields through a zirconocene- and CuCl-mediated intermolecular coupling process. This synthetic procedure involved three organic partners, including one CH2 I2 , and two different or identical alkynes. Two alkynes or one diyne undergo Cp2Zr(II)-mediated (Cp = η(5)-C5H5) pair-selective reductive coupling to afford the corresponding zirconacyclopentadiene derivatives, which react, in the presence of CuCl and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1 H)-pyrimidinone (DMPU), with CH2I2 through intermolecular followed by intramolecular coupling to afford the cyclopentadiene derivatives. An application of the prepared tetrasubstituted cyclopentadiene derivatives was demonstrated by the facile synthesis of the corresponding zirconocene complexes [((4R)Cp)2ZrCl2] and [((4R)Cp)2ZrR'2] (R' = Me, Et, or nBu). The unique 1,2,3,4-tetrasubstituted cyclopentadiene ligands and the corresponding metallocenes are expected to have further applications in organometallic chemistry and organic synthesis.

ChemInform Abstract: Assembly of Fused Indenes via Au(I)‐Catalyzed C1—C5 Cyclization of Enediynes Bearing an Internal Nucleophile.

AbstractA tandem reaction initiated by Au(I)‐catalyzed C1—C5 cyclization of enediynes (I) and (III) bearing an internal carboxy nucleophile is developed, providing a novel route for the assembly of fused indene derivatives (II) and (IV).

ChemInform Abstract: Gold Catalysis: Catalyst Oxidation State Dependent Dichotomy in the Cyclization of Furan—Yne Systems with Aromatic Tethers.

AbstractThis method yields either fluorene derivatives or 2‐furyl‐substituted indene derivatives depending on the applied gold catalyst.

Turn‐On Fluorogenic Probes for the Selective and Quantitative Detection of the Cyanide Anion from Natural Sources

We report new indene derivatives that are good fluorogenic probes for the cyanide anion, one of which is a highly selective and sensitive fluorogenic probe for the fluorescent detection--as well as reliable quantification--of the cyanide anion in water or buffer, with a 10(3)-fold increase of fluorescence and low detection limit. It is therefore useful for the quantification of natural cyanide from aqueous extracts of green almond seeds, thus proving that the system is suitable for fast detection and quantification of cyanide from natural sources.

Synthesis of Indene Frameworks via Rhodium-Catalyzed Cascade Cyclization of Aromatic Ketone and Unsaturated Carbonyl Compounds

A novel rhodium(III)-catalyzed direct functionalization of the ortho-C-H bond of aromatic ketone derivatives and an intramolecular cyclization sequence produced indene derivatives in moderate to good yields. This cascade cyclization involves a conjugate addition of α,β-unsaturated ketone and subsequent aldol condensation. The reaction occurred efficiently in the presence of water and under an atmosphere of air.

One-step synthesis of substituted isobenzofuran-1(3H)-ones and isobenzofuran-1,3-diones from indane derivatives in subcritical media

Molecular oxygen is one of the most attractive oxidants in organic synthesis because it is highly soluble in subcritical water. In this study, indane derivatives were oxidized to the corresponding isobenzofuran-1(3H)-one with molecular oxygen and isobenzofuran-1,3-dione with a mixture of molecular oxygen and H2O2 in subcritical water. This paper describes a simple, economic, environmentally benign,and general procedure that can be used for the synthesis of substituted isobenzofuran-1(3H)-ones and isobenzofuran-1,3-diones in only one step and without catalyst.

ChemInform Abstract: A Conjunctive Carboiodination: Indenes by a Double Carbopalladation—Reductive Elimination Domino Process.

AbstractThe method renders possible the preparation of various indene derivatives in good yields.

One-pot synthesis of indene derivatives by CF3SO3H-promoted reactions of benzylic alcohols and 1,3-dicarbonyl compounds

An efficient and convenient one-pot synthesis of indene derivatives was achieved in moderate to high yields by the CF3SO3H promoted coupling/cyclization reaction of benzylic alcohols and 1,3-dicarbonyls for the first time. For the reactions of methoxy- or methyl-substituted diarylmethanols with 1,3-dicarbonyls, 2equiv of CF3SO3H was needed to reach the best results; but for the reactions of methoxy-substituted arylethanols with 1,3-dicarbonyls, 0.6equiv of CF3SO3H at lower temperatures was capable of promoting the reaction finished.

FeCl3 Catalyzed Prins-Type Cyclization for the Synthesis of Highly Substituted Indenes: Application to the Total Synthesis of (±)-Jungianol and epi-Jungianol

A novel approach was developed for the synthesis of highly substituted indene derivatives, using an FeCl(3) catalyzed Prins-type cyclization reaction which was further applied in the total synthesis of jungianol and epi-jungianol.

Palladium-catalyzed insertion of α,β-unsaturated N-tosylhydrazones and trapping with carbon nucleophiles

Palladium-catalyzed carbene migratory insertion-cyclization reactions were reported, delivering dihydronaphthalene and indene derivatives in moderate to good yields. A three-component cross-coupling was also developed. The reactions are easy to handle, under mild conditions and various functional groups are tolerated.

Amine–N-heterocyclic carbene cascade catalysis for the asymmetric synthesis of fused indane derivatives with multiple chiral centres

An aminocatalytic asymmetric Diels-Alder reaction of 2,4-dienals and labile 1-indenones in situ generated from 3-bromo-1-indanones was developed, producing highly fused indane products with multiple chiral centres followed by a cascade N-heterocyclic carbene-mediated benzoin condensation.