- Preparation of 6α-Substituted Optically Pure Steroid with Thiophene as the A Ring via Assymetric Induction. A Circular Dichroism Study
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A number of assymetrically induced cyclization reactions are described, furnishing specifically substituted steroid-like systems with thiophene as the A ring.Ring closure of achiral compounds give two enantiomeric trans-anti-fused products, containing thr
- Macco, Anton A.,Buck, Henk M.
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Read Online
- Nickel-Catalyzed Ring Expansion of Cyclobutanones towards Indanones
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Despite recent advances in catalytic ring-opening/cross-coupling process of o-halogen tethered phenylcyclobutanones with other partners, single-component ring expansion of such precursors towards 3-methylindanones has not been disclosed. We present herein a nickel catalyzed C?C bond reconstruction sequence of o-bromophenylcyclobutanones using H2O as hydrogen donor, leading to a series of indanones, which can be further converted into other benzene-fused cyclic compounds.
- Chen, Tengyun,Wu, Yunkai,Han, Peilin,Gao, Jiqiang,Wu, Yuanqi,Zhao, Jinbo,Liang, Haotian,Liu, Yongsheng,Liu, Yu
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- Exploring the synthetic potential of a marine transaminase including discrimination at a remote stereocentre
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The marine transaminase, P-ω-TA, can be employed for the transamination from 1-aminotetralins and 1-aminoindanes with differentiation of stereochemistry at both the site of reaction and at a remote stereocentre resulting in formation of ketone products with up to 93% ee. While 4-substituents are tolerated on the tetralin core, the presence of 3- or 8-substituents is not tolerated by the transaminase. In general P-ω-TA shows capacity for remote diastereoselectivity, although both the stereoselectivity and efficiency are dependent on the specific substrate structure. Optimum efficiency and selectivity are seen with 4-haloaryl-1-aminotetralins and 3-haloaryl-1-aminoindanes, which may be associated with the marine origin of this enzyme. This journal is
- Schwarz, Maria,Murphy, Edel J.,Foley, Aoife M.,Woods, David F.,Castilla, Ignacio Abreu,Reen, F. Jerry,Collins, Stuart G.,O'gara, Fergal,Maguire, Anita R.
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supporting information
p. 188 - 198
(2021/01/18)
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- Preparation method of indanone compound
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The invention provides a preparation method of a hydrindone compound, and belongs to the technical field of compound synthesis. The method comprises the following steps: under the action of a nickel catalyst, a ligand, bis(pinacolato)diboron, alkali and water, reacting o-bromophenyl cyclobutanone of a formula 1 structure in a solvent at 70-90 DEG C for 12-24 hours, and separating and purifying a product after the reaction is finished to obtain the indanone compound of the formula I structure. The method is simple, raw materials are easy to obtain, experimental operation is simple and convenient, and the yield of the prepared product is moderate.
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Paragraph 0035-0081
(2021/08/07)
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- CAGED COMPOUND AND METHOD FOR PRODUCING THE SAME
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PROBLEM TO BE SOLVED: To provide a photoresponsive caged compound that can suppress biological damage and has excellent reaction efficiency, has water solubility, and can perform efficiently spatiotemporal control of bioactive substance such as amino acid
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Paragraph 0042
(2020/05/20)
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- One-pot multicomponent synthesis and antimicrobial evaluation of novel tricyclic indenopyrimidine-2-amines
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The synthesis of novel tricyclic indenopyrimidine-2-amines from 3,3-dimethyl-/3-methyl-2H-indanones has achieved by base-catalyzed one-pot three-component reaction. The desired products are formed within 10 hours after addition at reflux temperature. This
- Kaur, Navjot,Singh, Pratibha,Kaur, Pawandeep,Yadav, Ajar Nath,Singh, Karan
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p. 3622 - 3631
(2020/08/19)
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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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- CYCLIC TETRAMER COMPOUNDS AS PROPROTEIN CONVERTASE SUBTILISIN/KEXIN TYPE 9 (PCSK9) INHIBITORS FOR THE TREATMENT OF METABOLIC DISORDERS
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The disclosure relates to inhibitors of PCSK9 useful in the treatment of cholesterol lipid metabolism, and other diseases in which PCSK9 plays a role, having the Formula (I): or a pharmaceutically acceptable salt, hydrate, solvate, prodrug, stereoisomer, N-oxide, or tautomer thereof, wherein R1, R1, R1, R1, R1, R1, R1, R1, R1, X1, X2, and X3 are described herein.
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Paragraph 0636; 0638
(2020/06/16)
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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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- 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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supporting information
p. 5588 - 5591
(2016/11/17)
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- INDANE BISPHENOLS, POLYMERS DERIVED THEREFROM, AND METHODS OF USE THEREOF
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Disclosed herein are indane bisphenol monomer units, and polymers derived from such monomer units. Also disclosed herein are blends including such polymers, articles made from such polymers and blends, methods of using such monomers, polymers, and blends,
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Paragraph 0246-0247
(2014/03/25)
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- Cobalt-catalyzed enantioselective intramolecular hydroacylation of ketones and olefins
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Cobalt-chiral diphoshine catalytic systems promote intramolecular hydroacylation reactions of 2-acylbenzaldehydes and 2-alkenylbenzaldehydes to afford phthalide and indanone derivatives, respectively, in moderate to good yields with high enantioselectivities. The ketone hydroacylation did not exhibit a significant H/D kinetic isotope effect (KIE) with respect to the aldehyde C-H bond, indicating that C-H activation would not be involved in the rate-limiting step.
- Yang, Junfeng,Yoshikai, Naohiko
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supporting information
p. 16748 - 16751
(2015/02/05)
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- NOVEL COMPOUND, AND KINESIN SPINDLE PROTEIN INHIBITOR AND APPLICATION THEREOF
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A compound represented by the following General Formula (I): where, in General Formula (I), R1 and R2 each represent an alkyl group which may have a substituent, R3 represents the following General Formula (II) or (III), and R1 and R2 may be identical or different, where, in General Formulas (II) and (III), X represents a hydrogen atom or a halogen atom, R4 represents a methyl group, a dimethyl group or an oxygen atom, and * represents a binding position.
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- COMPOUND, KINESIN SPINDLE PROTEIN INHIBITOR, AND APPLICATION THEREOF
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A compound represented by the following General Formula (I): where, in General Formula (I), R1 and R2 each represent an alkyl group which may have a substituent, R3 represents the following General Formula (II) or (III), and R1 and R2 may be identical or different, where, in General Formulas (II) and (III), X represents a hydrogen atom or a halogen atom, R4 represents a methyl group, a dimethyl group or an oxygen atom, and * represents a binding position.
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- Facile synthesis of dihydrochalcones via the AlCl3-promoted tandem Friedel-Crafts acylation and alkylation of arenes with 2-alkenoyl chlorides
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Tandem Friedel-Crafts acylation and alkylation of arenes with 2-alkenoyl chlorides were investigated under the catalysis of Lewis acids. The cascade reaction affords dihydrochalcones in good yields accompanying 1-indanone derivatives in some cases, in the presence of anhydrous aluminum chloride. The scope, limitation, and mechanism of the tandem reaction were also explored. The intermolecular Friedel-Crafts alkylation for the formation of dihydrochalcones is more favorable than the intramolecular one for the generation of 1-indanones in the tandem reaction due to a stable six-membered ring transition state. The sequent process was further studied by the DFT computations at the M06-2X/6-31G(d) level, which are in great agreement with the experimental observation and support the proposed mechanism. The current method provides a convenient and economic method to synthesis of dihydrochalcones.
- Zhou, Yang,Li, Xinyao,Hou, Shili,Xu, Jiaxi
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p. 203 - 211
(2013/01/14)
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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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supporting information; scheme or table
p. 2939 - 2942
(2012/05/20)
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- Controlling chiral organization of molecular rods on Au(111) by molecular design
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Chiral self-assembled structures formed from organic molecules adsorbed on surfaces have been the subject of intense investigation in the recent decade, owing both to relevance in applications such as enantiospecific heterogeneous catalysis or chiral sepa
- Knudsen, Martin M.,Kalashnyk, Nataliya,Masini, Federico,Cramer, Jacob R.,Laegsgaard, Erik,Besenbacher, Flemming,Linderoth, Trolle R.,Gothelf, Kurt V.
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supporting information; experimental part
p. 4896 - 4905
(2011/05/16)
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- Synthesis of Chiral 3-Alkyl-3,4-dihydroisocoumarins by dynamic kinetic resolutions catalyzed by a Baeyer-Villiger Monooxygenase
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"Chemical Equation Presented" Baeyer-Villiger monooxygenases have been tested, in the oxidation of racemic benzofused ketones. When employing a single mutant of phenylacetone monooxygenase (M.446G PAMO) under the proper reaction conditions, it was possible to achieve 3-substituted 3,4-dihydroisocoumarins with, high yields and optical purities through regioselective dynamic kinetic resolution processes.
- Rioz-Martinez, Ana,De Gonzalo,Torres Pazmino, Daniel E.,Fraaije, Marco-W.,Gotor, Vicente
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supporting information; experimental part
p. 2073 - 2076
(2010/06/17)
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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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- Unique solvent effect on photochemistry of ortho-alkylphenacyl benzoates
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Photolysis of 2,4,6-trialkylphenacyl benzoates gives not only the corresponding indanones and benzoic acid, but also the corresponding benzocyclobutenols (CBs), which are also detected in the photolysis of mono-alkylphenacyl benzoates for the first time.
- Park, Bong Ser,Ryu, Hyuk Jun
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scheme or table
p. 1512 - 1516
(2010/04/29)
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- MACROCYCLIC GHRELIN RECEPTOR MODULATORS AND METHODS OF USING THE SAME
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The present invention provides novel conformationally-defined macrocyclic compounds that can function as selective modulators of the ghrelin receptor (growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, gastrointestinal disorders, cardiovascular disorders, obesity and obesity-associated disorders, central nervous system disorders, bone disorders, genetic disorders, hyperproliferative disorders and inflammatory disorders.
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Page/Page column 51
(2008/12/07)
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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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- 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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- 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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p. 7505 - 7507
(2008/03/14)
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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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- Asymmetric reduction of substituted indanones and tetralones catalyzed by chiral dendrimer and its application to the synthesis of (+)-sertraline
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A recoverable dendrimeric supported prolinol was used as a catalyst in the asymmetric reduction of indanones and tetralones to give separable cis and trans isomers up to 97% ee. This method was also applied in the enantioselective synthesis of the antidepressant drug (+)-sertraline.
- Wang, Guangyin,Zheng, Changwu,Zhao, Gang
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p. 2074 - 2081
(2007/10/03)
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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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p. 8391 - 9394
(2007/10/03)
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- Catalytic enantioselective Negishi reactions of racemic secondary benzylic halides
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This report describes the first enantioselective cross-couplings of racemic secondary benzylic halides, specifically, nickel-catalyzed Negishi reactions of bromides and chlorides. The catalyst components are commercially available and air-stable, and the reaction is not highly oxygen- or moisture-sensitive (it can be set up in the air). The method has been applied to the catalytic enantioselective synthesis of intermediates employed by others in the generation of bioactive compounds (e.g., trikentrin A and an androgen receptor agonist). Copyright
- Arp, Forrest O.,Fu, Gregory C.
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p. 10482 - 10483
(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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- Microwave-enhanced carbonylative generation of indanones and 3-acylaminoindanones
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(Chemical Equation Presented). The development of microwave-accelerated protocols for palladium(0)-catalyzed carbonylative cyclization of unsaturated aryl bromides and chlorides is described. By employing o-bromostyryl derivatives lacking substituents on the vinylic bond, molybdenum hexacarbonyl-mediated in situ carbonylation delivered a set of indan-1-one products in high yield after only 20 min of heating. Without the addition of the tri-tert-butylphosphine releasing Fu-salt ((t-Bu)3PHBF4), only incomplete conversions of sluggish o-styryl bromides and chlorides were realized. Internal and chemoselective palladium(0)-catalyzed Heck arylations of enamides afforded suitable starting materials for subsequent rapid ring-closing reactions. Microwave-heated intramolecular in situ carbonylation of these electron-rich and sterically congested olefins conveniently afforded eight functionalized 3-acylaminoindanone derivatives in a novel synthetic process. Attempted carbonylative annulation of electron-poor o-bromocinnamic acid derivatives furnished only the corresponding lactones via a competing hydroxycarbonylation- Michael addition reaction sequence.
- Wu, Xiongyu,Nilsson, Peter,Larhed, Mats
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p. 346 - 349
(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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- Photochemical preparation of highly functionalized 1-indanones
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A series of o-alkylphenyl alkyl ketones 1 were synthesized by different methods. The presence of a leaving group X adjacent to the carbonyl group is the special peculiarity of these ketones. Upon irradiation the keto carbonyl group of these compounds undergoes an n-π* excitation followed by a 1,5-hydrogen migration from the o-alkyl substituent to the carbonyl oxygen atom. The thus formed 1,4-diradicals are subject to a very rapid elimination of acid HX, giving 1,5-diradicals. We called this process spin center shift. After intersystem crossing these diradicals cyclize to 1-indanones 20 in good yields. Depending on the solvent and on substituents, o-alkoxyalkyl ketones 22 or benzo-[c]furanes 21 are obtained as byproducts. The mechanism of the cyclization was elucidated by quantum chemical calculations and kinetic measurements.
- Wessig, Pablo,Glombitza, Clemens,Mueller, Gunnar,Teubner, Janek
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p. 7582 - 7591
(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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- Efficient kinetic resolution in the asymmetric hydrosilylation of imines of 3-substituted indanones and 4-substituted tetralones
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Kinetic resolution of the N-methyl imines of 3-substituted indanones and 4-substituted tetralones could be accomplished by hydrosilylation with a chiral titanocene catalyst. N-Methyl imines of 4-substituted tetralones were resolved to yield, after hydrolysis of the unreacted starting materials, ketones with high ee's and the amine products with high diastereomeric and enantiomeric purity. The utility of this process was demonstrated in the synthesis of sertraline.
- Yun, Jaesook,Buchwald, Stephen L.
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p. 767 - 774
(2007/10/03)
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- New indenyl titanium catalysts for syndiospecific styrene polymerizations
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A series of multi-methyl-substituted indenes as well as allylindene, n-propylindene, n-but-1-enylindene, and n-butylindene have been prepared in good yields. The substituted indenes were converted into trimethylsilyl derivatives via reactions of intermediate organolithium complexes with chlorotrimethylsilane. The corresponding titanium complexes were synthesized in excellent yields from reactions of the trimethylsilyl derivatives with TiCl4. The titanium complexes were evaluated as styrene polymerization catalysts in toluene solution when activated by methylaluminoxane. In general, catalytic activities decreased with each additional methyl substituent. Syndiospecificities were very high (90-95%).
- Ready, Thomas E.,Chien, James C.W.,Rausch, Marvin D.
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- Total synthesis of (±)-iso-trans-trikentrin B
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The synthesis of the title compound, a member of a family of cyclopent[g]indoles isolated from a marine sponge, is described. Most of the synthetic sequence was developed starting from the more readily available cis-l,3-dimethylindan. An X-ray crystal structure of the indanol (24), the precursor of trns-1,3-dimethylindan, confirmed its relative stereochemistry.
- MacLeod, John K.,Ward, Annemarie,Willis, Anthony C.
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p. 177 - 187
(2007/10/03)
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- 6-Chloro-2,3-Dihydro-4H-1-Benzopyran Carboxylic Acids: Synthesis, Optical Resolution and Absolute Configuration
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6-Chloro-2,3-dihydro-4H-1-benzopyran-2-carboxylic acid, a rigid analogue of clofibric acid, the active metabolite of the antilipidemic drug clofibrate, has been prepared together with two isomers, 6-chloro-2,3-dihydro-4H-1-benzopyran-3- and 4-carboxylic a
- Loiodice, Fulvio,Longo, Antonio,Bianco, Pasquale,Tortorella, Vincenzo
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p. 1001 - 1012
(2007/10/03)
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- Heteroaryl piperazine antipsychotic agents
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Compounds of the formula STR1 and pharmaceutical compositions comprising them, wherein R1, Z, X, W and Y are as defined below. The compounds are useful in the treatment of psychosis and anxiety.
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- Preparation of chiral indanones and dihydrocoumarins; Application to synthesis of (+)-3-(2,6-dimethoxyphenyl) pentanoic acid
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Chiral β-aryl carboxylic acids, prepared by Michael addition of organocuprates to chiral unsaturated imides, are transformed into chiral 3- alkyl-4-benzoyloxyindan-1-ones via two intramolecular acylations, with intermediate formation of chiral 3-alkylindanones and corresponding dihydrocoumarins. The 3-(S)-ethyl-4-benzoyloxyindanone is transformed into(+)-3-(S)-(2,6-dimethoxyphenyl)pentanoic acid.
- Stephan,Rocher,Aubouet,Pourcelot,Cresson
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- An unusual C-C bond cleavage with chromium VI reagents: Oxidation of primary alcohols to ketones
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Oxidation of 1-hydroxymethylindanes and 1-hydroxymethyltetralins with PDC or PCC in methylene chloride affords 1-indanones and 1-tetralones.
- Bijoy,Subba Rao
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p. 2701 - 2708
(2007/10/02)
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- Dihydroindenoindole compounds and methods for using the same
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Compounds of the formula STR1 wherein R is hydrogen or a lower alkyl group, R1 and R2 are independently selected from hydrogen or a lower alkyl group, R3, R4 and R6 are independently selected from hydrogen, halogen or a lower alkyl group, R5 is hydrogen, hydroxy, halogen, a lower alkyl group, a lower alkoxy group, a mono- or di-lower alkylamino group, NH2 or NR11 COR12, R7, R8, R9 and R10 are independently selected from hydrogen, hydroxy, a lower alkyl group, a lower alkoxy group, a mono- or di-lower alkylamino group, NH2 or NR11 COR12, R11 is a hydrogen or a lower alkyl group, R12 is a lower alkyl group, with the proviso that when R is hydrogen then at least one of the substituents R1 to R10 is not hydrogen, or a salt thereof, are useful as antioxidants, within the medical and non-medical field, and that when R is hydrogen, methyl or neopentyl in formula IA, then at least one of R1 to R10 is not hydrogen. Many of the compounds of formula IA and IB are new and various methods for preparing them are described.
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- Heterocyclic systems containing bridgehead nitrogen atom: Part LXVII - reaction-of 3-methylspiro[indane-1,3'-hexahydro-s-tetrazine] -6'-thione with chloroacetic acid, α-and β-bromopropionic acids
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3-Methylspiro[indane-1,3'-hexahydro-s-tetrazine]-6'-thione (II), obtained from the reaction of 3-methylindan-1-one (1) with thiocarbohydrazide, on condensation with chloroacetic acid α- and β-bromopropionic acids results in the facile syntheses of 3-methy
- Sharma,Kumar,Pujari
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p. 440 - 442
(2007/10/02)
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- Convenient Synthetic Sequence for the Preparation of Indanones
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A convenient and general methods is reported for the synthesis of indanones from aryl ketones or aldehydes.
- Smonou, Ioulia,Orfanopoulos, Michael
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p. 1387 - 1397
(2007/10/02)
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- Reactions of Carboxylic Acids with "Phosphonium Anhydrides"
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General considerations are outlined for a reagent to extract oxygen from organic molecules by an equivalent of dehydration.Reagents, (R3P+)2O, 2OTf-, were created for the purpose and subjected to a preliminary study.They were found to convert carboxylic acids readily and rapidly to anhydrides, esters, amides, amidines, benzimidazoles, and cyclic aryl ketones in good yields.
- Hendrickson, James B.,Hussoin, Md. Sajjat
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p. 1144 - 1149
(2007/10/02)
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- Modern Friedel-Crafts chemistry XIII. Intra- and intermolecular cyclization of some carbonyl derivatives under Friedel-Crafts conditions
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Carbonyl group deactivation in the cycloalkylation of aryl haloalkyl ketones was studied.Ketones 1-5 were prepared and subjected to treatment with AlCl3, AlCl3/H2SO4 and H2SO4 catalysts.Whereas AlCl3 catalyst gave no cyclization products, the use of AlCl3/H2SO4 and H2SO4 catalysts afforded the corresponding indanones and/or tetralones (6-11).The intermediate p-methylacrylophenone (12) was also obtained in the case of ketone 2.Furthermore intermolecular cyclizations of benzene, toluene and p-xylene with 3-chloropropionyl chloride (13) and 4-chlorobutyryl chloride (14) were investigated.In the presence of AlCl3/CH3NO2 catalyst, only the corresponding aryl haloalkyl ketones (1-5) were formed whereas the use of AlCl3 catalyst gave, in addition, some cyclic ketones.However, the use of AlCl3/H2SO4 catalyst gave only the corresponding cyclic ketones (6-11).Results are discussed and mechanisms are suggested.In conclusion, carbonyl group deactivation for ring closure is demonstrated in the investigated ketones and cyclization can only effected under strenuous conditions.
- Khalaf, Ali A.,Abdel-Wahab, Aboel-Magd A.,El-Khawaga, Ahmed M.,El-Zohry, Maher F.
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p. 285 - 291
(2007/10/02)
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- REDUCTION PAR LE BOROHYDRURE DE SODIUM D'INDANONES CHROME TRICARBONYLE ENDO SUBSTITUEES EN α ET β. POSITION DE L'ETAT DE TRANSITION ET FACTEURS DE REACTIVITE
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In the indanone Cr(CO)3 series the substitution of the β endo hydrogen atom by alkyl groups has shown an increased reactivity towards NaBH4 reduction attributed to a deconjugation of carbonyl group.While in the endo α-substituted series, a decreased reactivity controlled by an enhancement of the activation enthalpy has been observed.The steric origin of this effect and its influence on the position of the transition state are discussed.
- Caro, B.,Jaouen, G.
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- Synthese de methoxycarbonylindenes, dihydro-1,2 naphtalenes et benzocycloheptene. Obtention des indanones-1, des tetralones-1 et de la benzosuberone correspondantes
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The synthesis of methoxycarbonylindenes, 1,2-dihydro-naphtalenes, and benzocycloheptene starting from the corresponding 1-indanones, 1-tetralones, and benzosuberone is reported.The starting ketones were synthesized by methods described in the literature which were optimized; in some cases new processes are described.
- Verbel, Joel,Carrie, Robert
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p. 116 - 124
(2007/10/02)
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- On the Absolute Configuration of (+)-Indane-1-carboxylic Acid
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The (R)-configuration, attributed to (+)-indane-carboxylic acid ((+)-1) by Fredga, is unequivocally confirmed (Scheme 1).Configurational doubts, raised by an erroneous ORD. curve of (-)-1-methylindane ((-)-4) published by Brewster and Buta, are unfounded (cf. the following paper of Brewster and the corrections in ).This was further verified by preparing deuteriated 1-methylindanes starting with (-)-(R)-3-phenylbutyric acid ((-)-(R)-5) as well as with (+)-(R)-1 or (-)-(S)-1 (Scheme 2).The ORD. curves of the optically active 4 thus obtained were (disregarding deuterium isotope effects) identical or antipodal, respectively (cf.Fig.1,2, and 7a-e).Optically active methyl indane-1-carboxylates ((-)-(R)-14 or (+)-(S)--14) show a strong solvent dependence of their ORD. and CD. spectra with a sign inversion occuring in going from isooctane to methanol or benzene.The observed changes can be explained by a change in the population of comformations where the ester carbonyl group is eclipsed either with the C(1),C(2)- or C(1),H-bond, with the n,?*-transition having a slightly different energy and the ester group an essentially enantiomeric environment with respect to its orientation relative to the benzene moiety.
- Hansen, Hans-Juergen,Sliwka, Hans-Richard,Hug, Werner
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p. 325 - 343
(2007/10/02)
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