- Synthesis method of indanone derivatives
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The present invention provides a synthesis method of indanone derivatives. The synthesis method comprises the following steps: adding a benzoic acid compound, an acrylate compound, a rhodium catalyst and an alkali to an organic solvent, heating under a nitrogen gas condition to carry out a reaction, and after the reaction is complete, carrying out post-treatment to obtain 2-substituted indanone compounds. According to the synthesis method of the indanone derivatives, one-step synthesis of the indanone products from the benzoic acid compound and the acrylic ester compound is realized; and the method is simple and convenient to operate, good in functional group compatibility and high in reaction yield.
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Paragraph 0064-0066; 0096-0098
(2021/06/13)
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- Synthesis method of 1-indanone compounds
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The present invention provides a synthesis method of 1-indanone compounds. The method comprises the following steps: adding benzoic acid compounds, dimethyl malonate, paraformaldehyde, a rhodium catalyst and an alkali to an organic solvent, heating under a nitrogen gas condition to carry out a reaction, and after the reaction is complete, carrying out post-treatment to obtain the 1-indanone compounds. The provided synthesis method of the 1-indanone compounds is simple and convenient to operate, the substrate is cheap and easy to obtain, wide in universality and good in functional group compatibility, and a simple and efficient method is provided for synthesizing indanone derivatives with diversified structures.
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Paragraph 0036-0047; 0048-0050
(2021/06/12)
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- Rh-Catalyzed Annulation of Benzoic Acids, Formaldehyde, and Malonates via ortho-Hydroarylation to Indanones
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A three-component reaction from readily available low-cost materials of benzoic acids, formaldehyde, and malonates for the preparation of indanones by rhodium catalysis is reported. The annulation is initiated by an ortho-hydroarylation of benzoic acids, and a Lewis acid is not required. The solvent has a significant influence to the reaction, and 2-substituted or nonsubstituted indanones are obtained by the change of solvent.
- Yu, Shuling,Lv, Ningning,Hong, Chao,Liu, Zhanxiang,Zhang, Yuhong
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p. 8354 - 8358
(2020/11/18)
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- Rhodium-Catalyzed Annelation of Benzoic Acids with α,β-Unsaturated Ketones with Cleavage of C?H, CO?OH, and C?C Bonds
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In the presence of a [Cp*RhCl2]2 catalyst, the Lewis acid In(OTf)3, and the mild base Na2CO3, aromatic carboxylates and α,β-unsaturated ketones undergo a unique hydroarylation/Claisen/retro-Claisen pr
- Zhang, Guodong,Hu, Zhiyong,Belitz, Florian,Ou, Yang,Pirkl, Nico,Goo?en, Lukas J.
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supporting information
p. 6435 - 6439
(2019/04/10)
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- Non-conventional methodologies in the synthesis of 1-indanones
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1-Indanones have been successfully prepared by means of three different non-conventional techniques, namely microwaves, high-intensity ultrasound and a Q-tube reactor. A library of differently substituted 1-indanones has been prepared via one-pot intramolecular Friedel-Crafts acylation and their efficiency and "greenness" have been compared.
- Oliverio, Manuela,Nardi, Monica,Costanzo, Paola,Cariati, Luca,Cravotto, Giancarlo,Giofre, Salvatore Vincenzo,Procopio, Antonio
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p. 5599 - 5610
(2014/06/10)
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- The design and synthesis of novel IBiox N-heterocyclic carbene ligands derived from substituted amino-indanols
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A synthetic route towards a number of novel IBiox N-heterocyclic carbene (NHC) ligands has been developed. The resulting ligands have restricted flexibility and high steric demand. Preliminary studies have shown these ligands to give high levels of asymmetric induction in the copper-free allylic alkylation of cinnamyl bromide.
- Levy, Jean-No?l,Latham, Christopher M.,Roisin, Lo?c,Kandziora, Nadine,Fruscia, Paolo Di,White, Andrew J. P.,Woodward, Simon,Fuchter, Matthew J.
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p. 512 - 515
(2012/02/04)
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- Asymmetric synthesis of chiral 1,3-diaminopropanols: Bisoxazolidine- catalyzed C-C bond formation with α-keto amides
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Three high-yielding steps lead to the formation of chiral 1,3-diaminopropanols from aliphatic and aromatic α-keto amides. In this approach, a nitroaldol reaction, which is catalyzed by Cu(SO2CF 3)2 and the bisoxazolidine ligand L1, is followed by two mild reduction reactions (see scheme). Laborious protection and deprotection steps can be avoided by using this method.
- Xu, Hanhui,Wolf, Christian
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p. 12249 - 12252
(2012/02/01)
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- SUBSTITUTED FLUOROETHYL UREAS AS ALPHA 2 ADRENERGIC AGENTS
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Therapeutic compounds, and methods, compositions, and medicaments related thereto are disclosed herein.
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Page/Page column 21
(2008/12/04)
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- Synthesis of indanones via solid-supported [2+2+2] cyclotrimerization
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(Chemical Equation Presented) A new facile approach toward natural and unnatural indanones has been developed, featuring a solid-supported [2+2+2] cyclotrimerization as the key step. This strategy has been applied to the chemo- and regioselective assembly of indanone arrays and to the total synthesis of a recently isolated indanone marine natural product.
- Senaiar, Ramesh S.,Teske, Jesse A.,Young, Douglas D.,Deiters, Alexander
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p. 7801 - 7804
(2008/03/11)
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- Meldrum's acids as acylating agents in the catalytic intramolecular Friedel-Crafts reaction
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(Chemical Equation Presented) The intramolecular Friedel-Crafts acylation of aromatics with Meldrum's acid derivatives catalyzed by metal trifluoromethanesulfonates is reported. Meldrum's acids are easily prepared, functionalized, handled, and purified. The synthesis of polysubstituted 1-indanones from benzyl Meldrum's acids was investigated thoroughly, and it was shown that a variety of catalysts were effective, while accommodating a diversity of functional groups under mild conditions. The scope, limitations, and functional group tolerance (terminal alkene and alkyne, ketal, dialkyl ether, dialkyl thioether, aryl methyl ether, aryl TIPS and TBDPS ethers, nitrile- and nitro-substituted aryls, alkyl and aryl halides) for a variety of 5-benzyl (enolizable Meldrum's acids) and 5-benzyl-5-substituted Meldrum's acids (quaternized Meldrum's acids), forming 1-indanones and 2-substituted-1- indanones, respectively, are delineated. This method was further applied to the synthesis of 1-tetralones, 1-benzosuberones, and the potent acetylcholinesterase inhibitor donepezil. Rate of cyclization as a function of ring size was established for various benzocyclic ketones via competition experiments: 1-tetralones form faster than both 1-indanones and 1-benzosuberones, and 1-benzosuberones cyclize faster than 1-indanones.
- Fillion, Eric,Fishlock, Dan,Wilsily, Ashraf,Goll, Julie M.
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p. 1316 - 1327
(2007/10/03)
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- Development of highly stereoselective asymmetric 6π- azaelectrocyclization of conformationally flexible linear 1-azatrienes. From determination of multifunctional chiral amines, 7-alkyl cis-1-amino-2-indanols, to application as a new synthetic strategy: Formal synthesis of 20-epiuleine
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The highly stereoselective asymmetric 6π-azaelectrocyclization was achieved as a general synthetic method based on the reaction between the (E)-3-carbonyl-2,4,6-trienal compounds and the (-)-7-alkyl-cis-l-amino-2-indanol derivatives which are effective chiral amines. The 7-alkyl-substituted 2-indanol moiety of the cyclized products was efficiently removed by the novel manganese dioxide oxidation under remarkably mild conditions, and the method was successfully applied to the formal synthesis of optically active 20-epiuleine.
- Tanaka, Katsunori,Kobayashi, Toyoharu,Mori, Hajime,Katsumura, Shigeo
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p. 5906 - 5925
(2007/10/03)
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- Synthesis of new chiral auxiliaries for 6π-azaelectrocyclization: 4- and 7-alkyl substituted cis-1-amino-2-indanols
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The synthesis of new chiral auxiliaries, 7-alkyl substituted cis-1-amino-2-indanol derivatives, was established by the Diels-Alder reaction of 1-substituted dienes with cyclopentenone followed by the asymmetric epoxidation of the resulting indene derivatives and then the Ritter reaction. These bulky cis-aminoindanol derivatives are very effective as chiral auxiliaries and nitrogen sources in the asymmetric 6π-azaelectrocyclization. The corresponding 4-alkyl derivative was also prepared using a similar method.
- Kobayashi, Toyoharu,Tanaka, Katsunori,Miwa, Junichi,Katsumura, Shigeo
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p. 185 - 188
(2007/10/03)
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- Indanylidenes. 1. Design and synthesis of (E)-2-(4,6-difluoro-1-indanylidene)acetamide, a potent, centrally acting muscle relaxant with antiinflammatory and analgesic activity
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The design of rigid cyclic analogues derived from cinnamamide 1, (E)-N-cyclopropyl-3-(3-fluorophenyl)prop-2-enamide, and β-methylcinnamamide 2, (E)-N-cyclopropyl-3-(3-fluorophenyl)but-2-enamide, has led to the discovery of the potent, centrally acting muscle relaxant (E)-2-(4,6-difluoro-1-indanylidene)acetamide, 17. Compound 17 also possesses potent antiinflammatory and analgesic activity. This paper describes the synthesis and the muscle relaxant, antiinflammatory, and analgesic structure-activity relationships of 17 and 67 of its analogues. Compound 17 has been taken into phase I clinical trials.
- Musso, David L.,Cochran, Felicia R.,Kelley, James L.,McLean, Ed W.,Selph, Jeffrey L.,Rigdon, Greg C.,Orr, G. Faye,Davis, Ronda G.,Cooper, Barrett R.,Styles, Virgil L.,Thompson, James B.,Hall, William R.
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p. 399 - 408
(2007/10/03)
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- Convenient Access to Polysubstituted 1-Indanones by Sc(OTf) 3-Catalyzed Intramolecular Friedel-Crafts Acylation of Benzyl Meldrum's Acid Derivatives
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(Matrix presented) The intramolecular Friedel-Crafts acylation of benzyl Meldrum's acids is catalyzed by Sc(OTf)3 under mild reaction conditions. Several polysubstituted 1-indanones have been prepared.
- Fillion, Eric,Fishlock, Dan
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p. 4653 - 4656
(2007/10/03)
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- Electron-transfer-induced tautomerization in methylindanones: Electronic control of the tunneling rate for enolization
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The radical cations generated from 4-methyl- and 4,7-dimethylindanone, as well as their deuterated isotopomers, isolated in Argon matrices, were found to undergo enolization to the corresponding enol radical cations at rates that differ by orders of magnitude. It is shown by quantum chemical calculations that the effect of the remote methyl group in the 4-position is of purely electronic nature in that it stabilizes the unreactive π-radical relative to the reactive σ-radical state of the 7-methylindanone radical cation. The observed kinetic behavior of the two compounds can be reproduced satisfactorily on the basis of calculated heigth and width of the thermal barrier for enolization, using the Bell model for quantum mechanical tunneling. High-level calculations on the methylacrolein radical cation show that barriers for enolization in radical cations are overestimated by B3LYP/6-31G*.
- Bednarek,Zhu,Bally,Filipiak,Marcinek,Gebicki
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p. 2377 - 2387
(2007/10/03)
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- An expeditious preparation of all enantiopure diastereoisomers of aromatic A-ring analogues of strigolactones, germination stimulants for seeds of the parasitic weeds Striga and Orobanche
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An expeditious manner to prepare all enantiopure diastereomers of aromatic A-ring strigolactone analogues is described. The racemic diastereoisomers of 8-methyl GR 24 and of its regioisomer 6-methyl GR 24 were prepared and separated, and subsequently chro
- Wigchert, Suzanne C. M.,Zwanenburg, Binne
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p. 2617 - 2623
(2007/10/03)
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- Integrated chemical process: One-pot aromatization of cyclic enones by the double elimination methodology
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A variety of aromatic hydrocarbons bearing multiple alkyl substituents are accessible with perfect regiocontrol in a one-pot reaction starting from cyclo-hexenones and their aromatic analogues [Eq. (1)]. The present methodology can be further extended to the synthesis of polycyclic aromatic hydrocarbons. The drawbacks encountered in the Friedel-Crafts reaction are resolved since the reaction proceeds under basic conditions.
- Orita, Akihiro,Yaruva, Jayamma,Otera, Junzo
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p. 2267 - 2270
(2007/10/03)
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- Synthesis and Na+/H+ exchange inhibitory activity of indanylideneacetylguanidines
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Synthesis of indanylideneacetylguadines 7a-i and their corresponding reduced compounds 8a-e has been achieved and their Na+/H+ exchange inhibitory activity evaluated. All the compounds studied exhibit significant inhibition of Na+/H+ exchanger activity. Promising activity is shown by compounds 7g, 8b and 8d. From the structure activity analysis, it appears that reduction of exocyclic double bond is associated with a marked increase in inhibitory activity.
- Ramakrishna,Jain,Ghate,Gupte,Vadlamudi
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p. 407 - 412
(2007/10/03)
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- An N.M.R. Investigation of the Mills-Nixon Effect
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The 4J coupling constant, previously established as a probe of bond order, was used to examine the bond orders in a series of ortho-bridged compounds: benzocyclopropene, 1,2-dihydrobenzocyclobutene, indan and tetralin.No evidence for sterically induced bond fixation (i.e. the Mills-Nixon effect) was found, but some evidence for electronic distortion in the corresponding benzylic ketones was observed.The experimental results are in accord with SCF/MO calculations.
- Collins, Michael J.,Gready, Jill E.,Sternhell, Sever,Tansey, Charles W.
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p. 1547 - 1557
(2007/10/02)
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- Benzoannelated Centropolyquinanes, 4. - Steric Effects in Multiply Substituted Triptindans (9H,10H-4b,9a-(Benzenomethano)indenoindenes)
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Upon cyclodehydration of-indanones 11, 12, and 14, the steric interactions of three substituents in the endo positions 4, 5, and 15 of triptindan (6) allow only one methyl group to be introduced into the molecular cavity.In accordance with DNMR measurements and molecular mechanical calculations of triptindans 1-5, this regioselectivity is caused by the considerably increased compression due to a second endo-methyl group in the triptindan rotamers A and A'.
- Paisdor, Bernd,Gruetzmacher, Hans-Friedrich,Kuck, Dietmar
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p. 1307 - 1314
(2007/10/02)
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- Steric Effects in the Synthesis of 1,7-Dialkylindans
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Synthesis routes to 1-alkyl(CH3,C2H5,i-C3H7)-6-methylindans and 1-alkyl(CH3,C2H5,i-C3H7)-7-methylindans are described.Members of the latter series, especially 1-isopropyl-7-methylindan, are sterically hindered through a peri interaction.This effect manifests itself throughout the study and necessitated use of alternative synthesis routes.Yields in the Grignard, Peterson olefination, Reformatsky, and Wittig reactions as well as catalytic hydrogenation and Li/NH3 reduction of α,β-unsaturated acids were compared.
- Budhram, Ronald S.,Palaniswamy, Ventakapuran A.,Eisenbraun, Edmund J.
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p. 1402 - 1406
(2007/10/02)
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- Photochemistry of α-oxo oximes. Part 9. The γ-hydrogen abstraction in α-oxo oxime ethers
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The photochemistry (λ 300 nm) of the α-oxo oxime ethers 1a and 2a has been studied with the objective of detecting any γ-H abstraction.Direct irradiation of (Z)-1a results only in (E)-(Z) isomerization, whereas direct irradiation of the isomeric α-oxo oxi
- Buys, Theo S. V.,Cerfontain, Hans,Geenevasen, Jan A. J.,Stunnenberg, Frank
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p. 188 - 194
(2007/10/02)
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- Stereopopulation Control. 8. Rate and Equilibrium Enhancement in the Formation of Homophthalic Anhydrides
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The kinetics of cyclization of α,α,3,4,6-pentamethylhomophthalic acid have been measured in sovent acetonitrile at 28.5 deg C, using as catalysts a series of acids ranging in strength from perchloric to acetic.In the presence of 0.12 M HClO4, t1/2 for acid anhydride formation = 0.3 s.For the stronger acid catalysts, kcycl is a linear function of catalyst concentration; for the weak acids, however, a change in rate-limiting step is revealed by curvature in the plots of ktotobsd vs. .All the weak acids show the same limiting value, 6.45E-3 min-1; this value is considered to be the rate constant for uncatalyzed formation of the tetrahedral intermediate.Homoconjugate bases (HA2(-)) of the weak acids show a similar curvature in their dilution plots, and the same limiting rate constant as for weak acids.Two independent and competitive pathways for cyclization are proposed.For strong acid catalysis, an intermediate acylium ion is considered on the basis of Broensted α = -0.79, kH/kD ca. 1, and acceleration of anhydride hydrolysis by methyl substituents.A value of ΔSexcit. = -23 eu suggests that cyclization, rather than acylium ion formation, is rate limiting.For weak acid catalysis, α = -0.17, kH/kD = 4.3, ΔSexcit. = -31 eu, and methyl groups retard anhydride hydrolysis by electron release; for this pathway, catalyzed breakdown of a tetrahedral intermediate is considered rate limiting.The composite Broensted plot is curved because the two pathways follow different rate laws.In contrast to rate enhancement results for phenolic lactone formation, the pentamethylhomophthalic acid is only sevenfold as reactive as α,α-dimethylhomophthalic acid.For the catalyst acids, pK(acetonitrile) is shown to be a linear function of pK(H2O) over the entire range of acids examined.
- Hillery, Paul S.,Cohen, Louis A.
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p. 2760 - 2770
(2007/10/02)
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- Carbon-13 Nuclear Magnetic Resonance Spectra of Pterosin-Sesquiterpenes and Related Indan-1-one Derivatives
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Methyl derivatives of indan-1-one were prepared as models to aid in interpreting the carbon-13 nuclear magnetic resonance ((13)C-NMR) spectra of pterosin-sesquiterpenes which were isolated from bracken fern, Pteridium aquilinum var. latiusculum.The chemical shifts of the carbons of the methylindan-1-ones were assigned by the proton decoupling technique.All the (13)C-NMR signals of the pterosin-sesquiterpenes were assigned by means of selective proton decouplings, and from the (13)C-(1)H long-range couplings and (13)C chemical shifts of the model compounds.Keywords - indan-1-one derivative; methylindan-1-one; pterosin-sesquiterpene; methylindan-1-one synthesis; (1)H-NMR; (13)C-NMR; selective decoupling; C-H decoupling
- Fukuoka, Masamichi,Yoshihira, Kunitoshi,Natori, Shinsaku,Mihashi, Kunihide,Nishi, Masatoshi
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p. 3113 - 3128
(2007/10/02)
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- Occupational medicine in Belgium
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In 1965 occupational medicine was extended to all Belgian industries. In view of the economical structure of the country, most of them became affiliated to occupational medical services. The supervision of workers' health and of the problems of industrial hygiene are the two main objectives of such a service.
- Brouwers
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p. 189 - 194
(2007/10/05)
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