- First synthesis of 1-phenyl-3-pyrrol-1-ylindan-2-carboxylic acid, a new scaffold of potential non-peptide endothelin receptor antagonists
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The first synthesis of trans, trans-1-phenyl-3-pyrrol-1-ylindan-2- carboxylic acid, a key-intermediate in the access to new potential non- peptide endothelin receptor antagonists, is reported.
- Guillon, Jean,Dallemagne, Patrick,Stiebing, Silvia,Bovy, Philippe R.,Rault, Sylvain
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- Formation of indanone from an iridanaphthalene complex
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The first example of evolution of an iridanaphthalene into an indanone through an intermediate indenyl is reported, serving as a good example of starting material to obtain indanones. Two new iridanaphthalenes are obtained by intramolecular C-H activation of a phenyl ring of a carbene ligand in [IrCp*{=C(OMe)CH=CPh2}(L)]PF6 (L = PPh 2Me, PMe3) complexes. It is demonstrated that these iridanaphthalene complexes can undergo a thermal reaction to give indenyl complexes and 3-phenylindanone.
- Talavera,Bolano,Bravo,Castro,Garcia-Fontan,Hermida-Ramon
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- Synthesis of 3-aryl-1-indanones via CsF-promoted coupling of arylboronic acids with N-tosylhydrazones
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A series of 17 3-aryl-1-indanones, four of which are novel, were prepared in good yield via a CsF-promoted reductive cross-coupling of the monotosylhydrazone of a 1,3-indanedione with an arylboronic acid. The method demonstrates wide substrate scope and good functional group tolerance. Moreover, the 3-aryl-1-indanones could also be prepared on a multi-gram scale.
- Liu, Yueqiang,Chen, Lingjuan,Liu, Yan,Liu, Ping,Dai, Bin
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- Superacidic and HUSY-zeolite activation of 1,3-indandione: reactions with benzene and cyclohexane
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1,3-Indandione (1) readily condenses with benzene and undergoes selective ionic hydrogenation with cyclohexane when activated by superacids, such as CF3SO3H, AlCl3 and AlBr3 to give 3,3-diphenyl-1-indanone (4) and 1-indanone (7), respectively. Combination of these reactions in 'one-pot' yields 3-phenyl-1-indanone (5). In addition, similar reactions have been carried out using the regenerable solid acid, HUSY-zeolite, providing an effective excess of acidic sites. The mechanism of these reactions, with potential involvement of superelectrophilic dicationic intermediates, is discussed.
- Koltunov, Konstantin Yu.
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- Rh(I)-catalyzed intramolecular hydroacylation in ionic liquids
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Rh(I)-catalyzed hydroacylation of 4-alkenal or 4,6-dienal using ionic liquids (ILs) as reaction media proceeded smoothly, giving cyclopentanone or cycloheptenone derivatives in good yields. It was found that the IL recovered after the reaction, which shou
- Oonishi, Yoshihiro,Ogura, Jiro,Sato, Yoshihiro
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- Gold-catalyzed formal cycloaddition of 2-ethynylbenzyl ethers with organic oxides and α-diazoesters
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A world of possibilities: Gold-catalyzed reactions of 2-ethynylbenzyl ethers with organic oxides and α-diazoesters gave 1,3-dihydroisobenzofuran and naphthalene derivatives, respectively (see scheme; EWG=electron-withdrawing group). Mechanisms for the formation of the formal cycloadducts were elucidated by isotope labeling. Copyright
- Pawar, Samir Kundlik,Wang, Chiou-Dong,Bhunia, Sabyasachi,Jadhav, Appaso Mahadev,Liu, Rai-Shung
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- Reactions of CF3-enones with arenes under superelectrophilic activation: A pathway to trans-1,3-diaryl-1-CF3-indanes, new cannabinoid receptor ligands
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4-Aryl-1,1,1-trifluorobut-3-en-2-ones ArCHCHCOCF3 (CF3-enones) react with arenes in excess of Bronsted superacids (TfOH, FSO3H) to give, stereoselectively, trans-1,3-diaryl-1-trifluoromethyl indanes in 35-85% yields. The r
- Iakovenko, Roman O.,Kazakova, Anna N.,Muzalevskiy, Vasiliy M.,Ivanov, Alexander Yu.,Boyarskaya, Irina A.,Chicca, Andrea,Petrucci, Vanessa,Gertsch, Jürg,Krasavin, Mikhail,Starova, Galina L.,Zolotarev, Andrey A.,Avdontceva, Margarita S.,Nenajdenko, Valentine G.,Vasilyev, Aleksander V.
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- Cyclization of 1-phenyl-2-propen-1-ones into 1-indanones using H-zeolite and other solid acids. The role of mono- and dicationic intermediates
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Cyclization of aryl vinyl ketones into 1-indanones was previously known to proceed only in drastic acidic or superacidic conditions due to the necessity of dicationic, superelectrophilic activation of starting compounds. In this paper, we disclose that available solid acids such as HUSY-zeolite, sulfated zirconia or heteropolyacid, H3PW12O40 can be successfully applied instead of superacids to perform these and related reactions. The cases, when the effective excess of acidic sites of the solid is required to carry out the reaction, are interpreted in terms of key dicationic (superelectrophilic) intermediates on the solid.
- Koltunov, Konstantin Yu.,Walspurger, Stéphane,Sommer, Jean
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- Versatile synthesis of 3-arylindan-1-ones by palladium-catalyzed intramolecular reductive cyclization of bromochalcones
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We have developed a novel and versatile synthesis of racemic 3-arylindan-1-ones by palladium-catalyzed intramolecular reductive cyclization of bromochalcones. This method is especially attractive because it avoids strong acidic conditions and consequently a larger number of sensitive functional groups are accepted during synthesis compared with existing methods.
- Pueschl, Ask,Rudbeck, Hans Christian,Faldt, Andre,Confante, Allesia,Kehler, Jan
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- Synthesis of Indanones and Spiroindanones by Diastereoselective Annulation Based on a Hydrogen Autotransfer Strategy
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An unprecedented nickel-catalyzed domino reductive cyclization of alkynes and o-bromoaryl aldehydes is described. The reaction features broad substrate scope and is tolerant of a variety of functional groups, providing straightforward access to biologically significant indanones and spiroindanone pyrrolidine derivatives in good yields with excellent regio- and diastereoselectivity. Preliminary mechanistic studies have shown that indanones are formed by the cyclization of o-bromoaryl aldehydes and alkynes to form indenol intermediates, followed by hydrogen autotransfer.
- Chen, Yate,Ding, Zhengtian,Wang, Yiming,Liu, Wenfeng,Kong, Wangqing
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supporting information
p. 5273 - 5278
(2021/02/03)
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- Construction of enantioenriched 9H-Fluorene frameworks via a cascade reaction involving remote vinylogous dynamic kinetic resolution
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The benzylic C-H group of α,α-dicyanoolefins from 3-substituted 1-indanones could be significantly activated via transmission along the aromatic system, thus enabling dynamic kinetic resolution via a traditional reversible deprotonation- protonation process. Enantioenriched 9-substituted 9H-fluorene frameworks were finally constructed through an asymmetric vinylogous Michael addition to nitroolefins, followed by a cascade cyclization and oxidative aromatization process, under the catalysis of a chiral bifunctional thiourea-tertiary amine.
- Hu, Cui-Xia,Chen, Lin,Hu, Di,Song, Xue,Chen, Zhi-Chao,Du, Wei,Chen, Ying-Chun
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supporting information
p. 8973 - 8977
(2020/11/30)
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- Palladium Nanoparticles-Catalyzed Synthesis of Indanone Derivatives via Intramolecular Reductive Heck Reaction
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An efficient protocol for the straightforward, single-step synthesis of 3-aryl-1-indanones from 2′-iodochalcone via reductive Heck reaction using phosphine free, stable and reusable binaphthyl stabilized palladium nanoparticle (Pd-BNP) as a catalyst has been described. An immense array of substrate scope with electron-rich and deficient 2′-iodochalcones have been synthesized. Further derivatization of product indanones have been achieved successfully. The heterogeneous nature of the Pd-BNP has been validated by centrifugation test and mercury poisoning experiment. Pd-BNP has been successfully recycled up to 5 cycles without any significant loss in reaction yield and particle size of nanoparticles, confirmed by TEM analysis. (Figure presented.).
- Parveen, Naziya,Sekar, Govindasamy
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p. 4581 - 4595
(2019/09/03)
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- Iridium-Catalyzed Synthesis of Substituted Indanones from Aromatic Carboxylates and Unsaturated Ketones
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A catalytic annulation is presented that provides straightforward, modular synthetic access to 3-substituted indanones from benzoic acids and α,β-unsaturated ketones. It is catalyzed by a bimetallic Ir/In system and proceeds via hydroarylation followed by
- Zhang, Guodong,Hu, Zhiyong,Bertoli, Giulia,Goo?en, Lukas J.
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p. 8153 - 8158
(2019/08/22)
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- Schmidt reaction on substituted 1-indanones / N-alkylation: Synthesis of benzofused six-membered ring lactams and their evaluation as antimicrobial agents
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Background: The presence of bicyclic lactams is reflected in various pharmaceuticals, natural products, agrochemicals and active components of various dyes. Nowadays, to see the increasing rate of antimicrobial resistance and high incidence of microbial infections, there is a strong need to develop novel antimicrobial agents. In this study, we synthesized some benzofused six membered ring lactams and their alkyl derivatives as a trial to obtain valuable precursors for the discovery of future an-timicrobial drugs. Methods: The substituted lactams 3,4-dihydro-2(1H)-quinolinones 3a-c and 3,4-dihydro-1(2H)-isoquinolinones 4a-c were synthesized by Schmidt reaction on indanones 2a-c which were obtained by Friedel-Crafts reaction on β-substituted α,β-unsaturated carboxylic acids 1a-c. Lactams 6 and 7 were obtained by N-alkylation on benzofused lactams 3a-c and 4a-c in good to excellent yields. Structures of all products were well characterized by the rigorous analysis of their IR,1H NMR,13C NMR, MS and elemental analysis. The in vitro antimicrobial activities of all the synthesized compounds 6 and 7 were determined against Gram-positive, Gram-negative bacteria and the fungal species Candida albi-cans using broth macrodilution method. Results: The Schmidt reaction of 3-methylindanone, 3-phenylindanone and 3,3-dimethylindanone using methane sulphonic acid was found to behave differently with respect to isolated yield as well as isomeric ratio of both lactams. Bacterial growth inhibition was observed with bicyclic lactam derivatives although their MIC values were higher than ampicillin. The significant inhibitory effects were shown by majority of compounds with MIC values 125-250 μg/ml. Antifungal activity of bicyclic lactam derivatives was observed against C. albicans. However, MICs values of all tested compounds were higher compared to standard antifungal agent miconazole. Conclusion: The four Schmidt experimental conditions were tried with the aim of achieving both 6-membered ring lactams in equal ratio and NaN3/MeSO3H was identified to fulfill our purpose. As evident by structure-activity relationship, the tested compounds have not resulted in superior antibacterial or anti-fungal compounds compared to standard antimicrobials. Hence, there is still a need to carry out further modifications in bicyclic lactams structure in order to more efficacious antimicrobial lead molecules.
- Arora, Rashi,Bala, Renu,Kumari, Poonam,Sood, Sumit,Yadav, Ajar Nath,Singh, Nasib,Singh, Karan
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p. 606 - 613
(2019/05/01)
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- Phosphine-Free and Reusable Palladium Nanoparticles-Catalyzed Domino Strategy: Synthesis of Indanone Derivatives
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The carbene migratory insertion involving a domino reaction by highly stable, reusable, and binaphthyl-stabilized Pd-nanoparticles (Pd-BNP) is disclosed. The reaction was catalyzed by 2 mol % of a heterogeneous Pd-BNP catalyst under external ligand-free c
- Saha, Rajib,Arunprasath, Dhanarajan,Sekar, Govindasamy
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p. 4692 - 4702
(2018/04/26)
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- Stereoselective construction of α-tetralone-fused spirooxindoles via Pd-catalyzed domino carbene migratory insertion/conjugate addition sequence
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An efficient diastereoselective synthesis of α- tetralone-fused spirooxindoles is reported. The Pd-catalyzed domino reaction proceeds through a carbene migratory insertion followed by a 6-endo-trig mode of conjugate addition sequence from easily accessibl
- Arunprasath, Dhanarajan,Bala, Balasubramanian Devi,Sekar, Govindasamy
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supporting information
p. 5280 - 5283
(2017/11/06)
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- A Weinreb Amide Based Building Block for Convenient Access to β,β-Diarylacroleins: Synthesis of 3-Arylindanones
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Towards the synthesis of symmetrical and unsymmetrical β,β-diarylacroleins for assembling diarylmethine fragments present in biologically important molecules, we have developed a new Weinreb amide (WA) based building block, derived from propiolic acid. The WA functionality present in this compound allowed the sequential addition of various arylmagnesium bromide reagents in a controlled manner. The developed methodology for the access to β,β-diarylacroleins has been utilised for the synthesis of biologically important 3-arylindanone molecules. Synthesis of both symmetrical and unsymmetrical β,β-diarylacrolein and diarylmethine fragments, have been achieved via easily accessible and hitherto unknown Weinreb Amide (WA) based building block 11. The WA functionality allowed the sequential addition of nucleophiles such as arylmagnesium bromide in a controlled manner, which has enabled the synthesis of an important 3-arylindanone molecule.
- Tiwari, Praveen Kumar,Aidhen, Indrapal Singh
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p. 2637 - 2646
(2016/06/08)
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- Asymmetric Induction in Hydroacylation by Cooperative Iminium Ion-Transition-Metal Catalysis
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A new strategy for the rhodium-catalyzed enantioselective hydroacylation is described. This has been achieved through the merger of iminium ion catalysis and transition-metal catalysis such that asymmetric induction derives from a readily accessible, inexpensive chiral nonracemic secondary amine catalyst rather than a chiral nonracemic phosphine as is typical of conventional asymmetric hydroacylation methods.
- Rastelli, Ettore J.,Truong, Ngoc T.,Coltart, Don M.
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p. 5588 - 5591
(2016/11/17)
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- different nuclear ruthenium palladium double-ring metal compound and its preparation method and application
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The invention discloses a heteronuclear ruthenium palladium bicyclic metal compound and a preparation method and an application thereof and belongs to the technical field of organic synthesis. The metal compound is easily prepared and modified, stable in
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Paragraph 0071; 0072
(2016/10/07)
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- Gold(I)-Catalyzed Addition of Silylacetylenes to Acylsilanes: Synthesis of Indanones by C-H Functionalization through a Gold(I) Carbenoid
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A gold(I)-catalyzed synthesis of indanones from trimethylsilylacetylenes and acylsilanes is presented. The reaction is initiated through a synergistic acylsilane activation-gold acetylide formation and involves consecutive alkyne σ-gold(I) addition, π-activation, and 1,2-migration of a silyl group. Studies performed on the reaction mechanism allowed to establish the nature of the silyl migrating group and invoke the participation of a gold(I) carbenoid intermediate. The reaction is completed by a gold(I) C-H functionalization step.
- González, Jairo,Santamaría, Javier,Ballesteros, Alfredo
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supporting information
p. 13678 - 13681
(2015/11/16)
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- Palladium-Catalyzed Intermolecular Carbene Insertion Prior to Intramolecular Heck Cyclization: Synthesis of 2-Arylidene-3-aryl-1-indanones
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A domino process that converges the migratory insertion of carbene with a Heck reaction has been established as a versatile tool for the synthesis of 2-arylidene-3-aryl-1-indanones from very stable and easily accessible N-tosylhydrazones and 2′-iodochalco
- Arunprasath, Dhanarajan,Muthupandi, Pandi,Sekar, Govindasamy
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p. 5448 - 5451
(2015/11/18)
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- Recent developments in the chemistry of heteroaromatic N -oxides
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Selected developments in the chemistry of heteroaromatic N-oxides since 2001 are presented in this review. The use of these N-oxides, both in late-transition-metal-catalyzed oxidations of carbon-carbon triple bonds and in regioselective C-H functionalizations of the heteroarene, are contemporary topics of interest and the focus of the discussion. 1 Introduction 2 Synthesis of Heteroaromatic N-Oxides 2.1 Direct Oxidation of Hindered Heteroarenes 2.2 Through Construction of Heteroaromatic Rings 3 Heteroaromatic N-Oxides as Oxidants 3.1 Alkyne Oxidation 3.2 Allene Oxidation 3.3 Carbene Oxidation 4 Heteroaromatic N-Oxides as Substrates 4.1 Deoxygenative ortho-C-H Functionalization with Prior Activation 4.2 Deoxygenative ortho-C-H Functionalization with Nonstabilized Carbanions 4.3 Nondeoxygenative C-H Functionalization 4.3.1 ortho-C-H Functionalization 4.3.2 N-Oxide Directed ortho-Alkyl C-H Functionalization 4.3.3 N-Oxide Directed Remote C-H Functionalization 4.4 1,3-Dipolar Cycloaddition 5 Conclusion and Outlook.
- Wang, Youliang,Zhang, Liming
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- Palladium-catalyzed asymmetric reductive Heck reaction of aryl halides
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Asymmetric reductive Heck reaction of aryl halides is realized in high stereoselectivity. Hydrogen-bond donors, trialkylammonium salts in a glycol solvent, were used to promote halide dissociation from neutral arylpalladium complexes to access cationic, stereoselective pathways.
- Yue, Guizhou,Lei, Kaining,Hirao, Hajime,Zhou, Jianrong
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supporting information
p. 6531 - 6535
(2015/06/08)
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- Simple, copper(I)-catalyzed oxidation of benzylic/allylic alcohols to carbonyl compounds: Synthesis of functionalized cinnamates in one pot
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An environmentally benign [Cu(I)]-catalyzed oxidation of activated (benzylic/allylic) alcohols to the corresponding carbonyl compounds is presented. Interestingly, the reaction was also compatible with benzylic alcohols containing ortho-bromo substituents on the aromatic ring without competing with the expected intermolecular Buchwald coupling. Significantly, the catalytic system enables the synthesis of cinnamate-esters in a sequential domino one-pot fashion via oxidation followed by Wittig-Horner protocol. Copyright
- Reddy, Alavala Gopi Krishna,Mahendar, Lodi,Satyanarayana, Gedu
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supporting information
p. 2076 - 2087
(2014/07/07)
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- Gold-catalyzed carboalkoxylations of 2-ethynylbenzyl ethers to form 1- and 2-indanones chemoselectively: Effects of ligands and solvents
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The selective syntheses of 1- and 2-indan-one compounds from 2-ethynylbenzyl ethers have been achieved with suitable catalysts and solvents. The highly acidic [tris(pentafluorophenyl)phos-phine]gold hexafluoroantimonate [(C6F5)3AuSbF6] in nitromethane (MeNO2) preferably gives 1-indan-ones whereas [(ortho-biphenyl) di(tert-butyl)phosphine] gold triflimide [(tBu)2(o-biphenyl) AuNTf2] in dichloroethane tends to form 2-indanone derivatives. For 2-indanone products, we isolated two indenyl methyl ethers for deuterium labeling analyses, providing evidence for p-alkyne activation.
- Wang, Chiou-Dong,Hsieh, Yi-Feng,Liu, Rai-Shung
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supporting information
p. 144 - 152
(2014/03/21)
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- AROMATIC KETONE SYNTHESIS WITH AMIDE REAGENTS AND RELATED REACTIONS
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A method of preparing an aryl carbonyl or aryl thiocarbonyl compound, comprises reacting an N-(nitroaryl)-amide or N-(nitroaryl)-thioamide with an aromatic ring, with a superacid catalyst, to produce the aryl carbonyl or aryl thiocarbonyl compound. The superacid is present in an amount of at most 8 equivalents in proportion to the N-(nitroaryl)-amide or N-(nitroaryl)-thioamide. A method of preparing aryl amide or aryl thioamide, comprises reacting an N-(nitroaryl)-carbamide or N-(nitroaryl)-thiocarbamide with an aromatic ring, with a superacid catalyst, to produce the aryl amide or aryl thioamide.
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Paragraph 0038; 0040
(2013/10/22)
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- Superacid-promoted dual C-C bond formation by Friedel-Crafts alkylation and acylation of ethyl cinnamates: Synthesis of indanones
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A superacid (triflic acid) promoted dual C-C bond formation via intermolecular Friedel-Crafts alkylation (Michael addition type) and intramolecular acylation for the efficient synthesis of 3-substituted indan-1-ones is presented. This method was successful in activating ethyl cinnamates towards dual aromatic electrophilic substitution. Moreover, it enabled us to synthesize novel spirotetracyclic systems. Georg Thieme Verlag Stuttgart · New York.
- Venkat Ramulu, Bokka,Gopi Krishna Reddy, Alavala,Satyanarayana, Gedu
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supporting information
p. 868 - 872
(2013/05/22)
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- Friedel-crafts acylation with amides
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Friedel-Crafts acylation has been known since the 1870s, and it is an important organic synthetic reaction leading to aromatic ketone products. Friedel-Crafts acylation is usually performed with carboxylic acid chlorides or anhydrides, while amides are generally not useful substrates in these reactions. Despite being the least reactive carboxylic acid derivative, we have found a series of amides capable of providing aromatic ketones in good yields (55-96%, 17 examples). We propose a mechanism involving diminished C-N resonance through superelectrophilic activation and subsequent cleavage to acyl cations.
- Raja, Erum K.,Deschepper, Daniel J.,Nilsson Lill, Sten O.,Klumpp, Douglas A.
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experimental part
p. 5788 - 5793
(2012/07/30)
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- Gold-catalyzed oxidative cyclizations of cis-3-En-1-ynes to form cyclopentenone derivatives
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Golden tendencies: The title reaction for synthesizing cyclopentenone derivatives utilizes a gold complex and 8-methylquinoline oxide as the catalyst system (see scheme; IPr=1,3-bis(diisopropylphenyl)imidazol-2-ylidene). Such products are not attainable using diazocarbonyl reagents, as the gold carbenoids tend to react with C-H bonds. Copyright
- Bhunia, Sabyasachi,Ghorpade, Satish,Huple, Deepak B.,Liu, Rai-Shung
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p. 2939 - 2942
(2012/05/20)
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- Synthesis of optically pure 1-amino-3-aryl indanes exemplified by (+)-indatraline
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A versatile procedure for the synthesis of optically pure 1-amino-3-aryl indanes is presented, exemplified by the synthesis of the triple uptake inhibitor (+)-indatraline (1). Georg Thieme Verlag Stuttgart · New York.
- N?rager, Niels Gr?n,Lorentz-Petersen, Linda Luise Reeh,Lyngs?, Lars Ole,Kehler, Jan,Juhl, Karsten
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p. 1753 - 1755
(2011/09/16)
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- Gold-catalyzed oxidative cyclization of 1,5-enynes using external oxidants
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Golden circle: Two gold-catalyzed oxidative cyclizations of 1,5-enynes using 8-methylquinoline N-oxide are presented (see example). Experimental results indicate that both reactions proceed through prior oxidation of alkyne to form α-carbonyl intermediate
- Vasu, Dhananjayan,Hung, Hsiao-Hua,Bhunia, Sabyasachi,Gawade, Sagar Ashok,Das, Arindam,Liu, Rai-Shung
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supporting information; experimental part
p. 6911 - 6914
(2011/09/12)
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- Synthesis of C3- and C2-symmetric tris- and bis-sulfoxide ligands by asymmetric oxidation
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A series of tris- and bis-sulfoxides were synthesized by multiple asymmetric oxidation of the corresponding sulfides. High enantioselectivities were obtained based on Horeau-type amplification of selectivity. Naphthyl-substituted sulfoxides allowed for higher selectivity and greater ease of purification. These sulfoxides were tested as ligands in rhodium-catalyzed olefin hydroacylation and 1,4-addition of phenyl boronic acid to 2-cyclohexen-1-one. While no enantioinduction was observed in hydroacylation, up to 80% ee was obtained for a tris-sulfoxide and a bis-sulfoxide ligand in the 1,4-addition. Bis-sulfoxides with flexible backbones gave lower and inversed enantioselectivity, suggesting backbone rigidity plays a key role in enantioinduction.
- Dornan, Peter K.,Leung, Priscilla L.,Dong, Vy M.
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experimental part
p. 4378 - 4384
(2011/08/04)
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- BTISA-catalyzed Friedel-Crafts bimolecular cyclization of cinnamic acid under superelectrophilic solvation conditions
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Friedel-Crafts bimolecular cyclizations of cinnamic acid and cinnamoyl chloride with aromatic compounds in strong and superstrong acids in present of 1 mol% BTISA were investigated. It was demonstrated that catalytic amounts of this new superacid have essential effect on such type of reactions. Its use makes possible the preparation of indanones with quantitative yields.
- Posternak, Anna G.,Garlyauskayte, Romute Yu.,Yagupolskii, Lev M.
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experimental part
p. 274 - 277
(2010/04/30)
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- Efficient entry into 2-substituted tetrahydroquinoline systems through alkylative ring expansion: Stereoselective formal synthesis of (±)-martinellic acid
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(Chemical Equation Presented) A new efficient synthesis of 2-substituted tetrahydroquinolines has been achieved by the domino reaction of N-indanyl(methoxy)amines, which consists of three types of reactions: elimination of an alcohol, the rearrangement of an aryl group, and the addition of an organolithium or magnesium reagent. The synthetic utility of this approach is demonstrated by the stereoselective formal synthesis of (±)- martinellic acid.
- Ueda, Masafumi,Kawai, Sayuri,Hayashi, Masataka,Naito, Takeaki,Miyata, Okiko
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experimental part
p. 914 - 921
(2010/06/16)
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- TREATMENT OF NEURODEGENERATIVE DISEASES USING INDATRALINE ANALOGS
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Methods and compositions useful in the treatment or prevention of synucleinopathies, such as Parkinson''s disease, diffuse Lewy body disease, and multiple system atrophy, or other neurodegenerative diseases (e.g., amyotrophic lateral sclerosis, Huntington''s disease, and Alzheimer''s disease) are provided. The treatment including administering to a subject an indatraline derivative that inhibits the aggregation of a-synuclein.
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Page/Page column 120
(2009/04/25)
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- Rhodium catalyzed reaction of internal alkynes with organoborons under CO atmosphere: a product tunable reaction
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Alkynes react with organoborons under a CO atmosphere in the presence of a rhodium(I) catalyst to afford mainly 5-aryl-2(5H)-furanones, α,β-unsaturated ketones, and indanones. The product selectivity can be tuned by modifying the reaction conditions.
- Artok, Levent,Ku?, Melih,Aksin-Artok, ?zge,Dege, Fatma Nurcan,?zkilin?, Fatma Yelda
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experimental part
p. 9125 - 9133
(2010/01/16)
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- [(NHC)AuCl]-catalyzed Meyer-Schuster rearrangement: scope and limitations
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An efficient catalytic system allowing for the synthesis of a variety of α,β-unsaturated ketones has been developed. [(NHC)AuCl] (NHC{double bond, long}N-heterocyclic carbene) in the presence of a silver(I) salt was found to catalyze the Meyer-Schuster rearrangement, leading to α,β-unsaturated ketones from easily accessible propargylic alcohols in high yields. Catalysis was performed in a 2:1 mixture of methanol and water at 60 °C and afforded good yields even for tertiary alcohols and sterically demanding substrates. Thorough evaluation of the present catalytic system uncovered that it was unsuitable for terminal alkynes and primary alcohols. In these cases low yields of the target molecules were obtained due to the formation of unexpected by-products.
- Ramón, Rubén S.,Marion, Nicolas,Nolan, Steven P.
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experimental part
p. 1767 - 1773
(2009/06/18)
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- Mild, efficient friedel-Crafts acylations from carboxylic acids using cyanuric chloride and AlCl3
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(Chemical Equation Presented) A mild method for Friedel-Crafts acylation with aromatic and aliphatic carboxylic acids using cyanuric chloride, pyridine, and AlCl3 was developed. Both inter- and intramolecular acylations were achieved at room temperature in high yield and in very short reaction times.
- Kangani, Cyrous O.,Day, Billy W.
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supporting information; experimental part
p. 2645 - 2648
(2009/05/27)
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- Solvent-dependent behavior of arylvinylketones in HUSY-zeolite: a green alternative to liquid superacid medium
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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.
- Sani Souna Sido, Abdelkarim,Chassaing, Stefan,Kumarraja, Mayilvasagam,Pale, Patrick,Sommer, Jean
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p. 5911 - 5914
(2008/02/10)
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- Zeolite-directed cascade reactions: Cycliacyarylation versus decarboxyarylation of α,β-unsaturated carboxylic acids
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The interaction of α,β-unsaturated carboxylic acids with benzene derivatives was investigated in H-zeolites and led to two distinct but competing processes, cycliacyarylation and decarboxyarylation. Interestingly, H-USY selectively induced the cycliacyarylation cascade reaction, whereas H-ZSM5 selectively promoted the decarboxyarylation cascade.
- Chassaing, Stefan,Kumarraja, Mayilvasagam,Pale, Patrick,Sommer, Jean
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p. 3889 - 3892
(2008/02/11)
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- Microwave-assisted one-pot synthesis of 1-indanones from arenes and α,β-unsaturated acyl chlorides
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A series of 1-indanones were synthesized in good yields via tandem Friedel-Crafts acylation and Nazarov cyclization of arenes and α,β-unsaturated acyl chlorides in the presence of aluminum chloride under microwave irradiation.
- Yin, Wei,Ma, Yuan,Xu, Jiaxi,Zhao, Yufen
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p. 4312 - 4315
(2007/10/03)
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- Synthesis and characterisation of some novel indeno[1,2-c]pyrazoles
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1-(Benzothiazol-2-yl)-4-phenylindeno[1,2-c]pyrazoles (1) and 1-(4-arylthiazol-2-yl)-4-phenylindeno[1,2-c]pyrazoles (2) have been synthesised by the reaction between 1-oxo-3-phenylindan-2-carboxaldehyde (4) and 2-hydrazinobenzothiazoles or 2-hydrazinothiazoles.
- Singh, Karan,Sharma, Pawan K.,Dhawan,Singh, Shiv P.
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p. 526 - 529
(2007/10/03)
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- Hydroacylation of 2-vinyl benzaldehyde systems: An efficient method for the synthesis of chiral 3-substituted indanones
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Asymmetric rhodium-catalyzed hydroacylation has been utilized in the synthesis of 3-substituted indanones with high conversions and enantioselectivity. The hydroacylation reaction of 2-vinyl benzaldehyde had been previously reported to give a low yield of indanone and an unidentified product. We have identified this compound as a dimer of the starting material. Substitution at the α-position of the 2-vinyl benzaldehyde substrates blocks the competitive dimerization reaction and allows the reaction to proceed with yields generally greater than 90%. Utilization of BINAP as a chiral ligand results in good chemical yields and enantioselectivity greater than 95% in most cases. Copyright
- Kundu, Kousik,McCullagh, James V.,Morehead Jr., Andrew T.
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p. 16042 - 16043
(2007/10/03)
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- Rh(I)-catalyzed cyclization of 1-arylprop-2-yn-1-ol derivatives utilizing rhodium 1,4-migration
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A highly useful method for the construction of cyclopentanone derivatives fused with aromatic ring based on hydrorhodation-1,4-rhodium migration sequence is achieved. Treatment of 1-aryl-prop-2-yn-1-ols, which are easily accessible via an addition of acetylides to the corresponding aryl aldehydes, with a catalytic amount of [Rh(cod)2]2(BF4) and P(p-tolyl)3 in the presence of a base gives cyclopentanone derivatives in moderate to good yield. Copyright
- Yamabe, Hokuto,Mizuno, Akio,Kusama, Hiroyuki,Iwasawa, Nobuharu
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p. 3248 - 3249
(2007/10/03)
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- Superacid-Catalyzed Reactions of Cinnamic Acids and the Role of Superelectrophiles
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The chemistry of cinnamic acids and related compounds has been studied. In superacid-catalyzed reactions with arenes, two competing reaction mechanisms are proposed. Both mechanisms involve the formation of dicationic intermediates (superelectrophiles), and the reactions can lead to either chalcone-type products or indanone products. The direct observation of a dicationic species (by low-temperature 13C NMR) is reported. We provide clear evidence that protonated carboxylic acid groups (or the corresponding acyl cation) can enhance the reactivity of an adjacent electrophilic center. Triflic acid is also found to be an effective acid catalyst for the direct synthesis of some electron-deficient chalcones and heterocyclic chalcones from cinnnamic acids.
- Rendy, Rendy,Zhang, Yun,McElrea, Aaron,Gomez, Alma,Klumpp, Douglas A.
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p. 2340 - 2347
(2007/10/03)
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- Synthesis of 1-indanones by intramolecular Friedel-Crafts reaction of 3-arylpropionic acids catalyzed by Tb(OTf)3
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Intramolecular Friedel-Crafts acylation reaction of 3-arylpropionic acids was efficiently catalyzed by Tb(OTf)3 at 250°C to give 1-indanones. Even deactivated 3-arylpropionic acids with halogen atoms on the aromatic ring can be cyclized in moderation to good yields.
- Cui, Dong-Mei,Zhang, Chen,Kawamura, Masato,Shimada, Shigeru
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p. 1741 - 1745
(2007/10/03)
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- Dicationic intermediates involving protonated amides: Dual modes of reactivity including the acylation of arenes
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Matrix presented. In the Bronsted superacid CF3SO 3H (triflic acid), amides are able to form reactive, dicationic electrophiles. It is shown that these dicationic intermediates participate in two distinctly different types of electrophilic reactions. The protonated amide increases the reactivity of an adjacent electrophilic group, and the protonated amide group itself shows enhanced reactivity arising from an adjacent cationic charge. In the latter case, several types of amides are even capable of reacting with benzene by Friedel-Crafts acylation.
- Klumpp, Douglas A.,Rendy, Rendy,Zhang, Yun,Gomez, Alma,McElrea, Aaron
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p. 1789 - 1792
(2007/10/03)
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- 1,3-disubstituted indene complexes
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The present invention relates to organometallic compounds of transition metals with an indenyl ligand bonded in the 2-position and substituted in the 1,3-position, a process for their production, and their use as catalysts for the (co)polymerization of ol
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- Palladium-catalyzed carbonylative cyclization of unsaturated aryl iodides and dienyl triflates, iodides, and bromides to indanones and 2-cyclopentenones
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Indanones and 2-cyclopentenones have been successfully prepared in good to excellent yields by the palladium-catalyzed carbonylative cyclization of unsaturated aryl iodides and dienyl triflates, iodides, and bromides, respectively. The best results are obtained by employing 10 mol % of Pd(OAc)2, 2 equiv of pyridine, 1 equiv of n-Bu4NCl, 1 atm of CO, a reaction temperature of 100 °C, and DMF as the solvent. This carbonylative cyclization is particularly effective on substrates that contain a terminal olefin. The proposed mechanism for this annulation includes (1) Pd(OAc)2 reduction to the active palladium(0) catalyst, (2) oxidative addition of the organic halide or triflate to Pd(0), (3) coordination and insertion of carbon monoxide to produce an acylpalladium intermediate, (4) acylpalladation of the neighboring carbon-carbon double bond, (5) reversible palladium β-hydride elimination and re-addition to form a palladium enolate, and (6) protonation by H2O to produce the indanone or 2-cyclopentenone.
- Gagnier, Steve V.,Larock, Richard C.
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p. 4804 - 4807
(2007/10/03)
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- Synthesis of a novel class of non-peptide NK-2 receptor ligand, derived from 1-phenyl-3-pyrrol-1-ylindan-2-carboxamides
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A series of trans,trans-1-phenyl-3-pyrrol-1-ylindan-2-carboxamide derivatives has been synthesized in eight steps starting from cinnamic acid or 3,3-diphenylpropionic acid. The trans,trans configuration of these carboxamides has been established by X-ray analysis and by NOE experiments in NMR. These new compounds were evaluated for their potential NK-1, NK-2 and NK-3 receptors binding affinity. The N,N-disubstituted carboxamides bound selectively on NK-2 receptors. Copyright
- Guillon, Jean,Dallemagne, Patrick,Leger, Jean-Michel,Sopkova, Jana,Bovy, Philippe R,Jarry, Christian,Rault, Sylvain
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p. 1043 - 1050
(2007/10/03)
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