- Synthesis and properties of macroheterocyclic compounds containing 1-imino-2-phenyl-1H-inden-3-amine fragments
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Reaction of 1-imino-2-phenyl-1H-inden-3-amine with 3,3′-dichloro-, 2,2′-disulfo-, and 2,2′-dinitrobiphenyl-4,4′-diamines gave 2: 1 and 1: 2 linear condensation products and symmetrical macroheterocycles. The products were characterized by the IR, UV, and
- Berezina,Fomina
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Read Online
- Palladium-Catalyzed Direct α-Arylation of Indane-1,3-dione to 2-Substituted Indene-1,3-diones
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A straightforward and feasible palladium-catalyzed direct α-arylation of indane-1,3-dione to 2-substituted aryl/heteroaryl indene-1,3-diones has been disclosed for the first time. Optimization of reaction conditions identified tBu-XPhos as a preferred ligand for the bis(acetonitrile)dichloropalladium(II) catalyst. A broad spectrum of aryl iodides and aryl triflates containing electron-donating, electron-withdrawing, and sterically hindered substituents gave an excellent yield for the quick access α-arylated 1,3-diones library.
- Hallur, Gurulingappa,Suresh, Palaniswamy,Tamizharasan, Natarajan
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p. 12318 - 12325
(2021/09/07)
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- Third-Generation Light-Driven Symmetric Molecular Motors
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Symmetric molecular motors based on two overcrowded alkenes with a notable absence of a stereogenic center show potential to function as novel mechanical systems in the development of more advanced nanomachines offering controlled motion over surfaces. Elucidation of the key parameters and limitations of these third-generation motors is essential for the design of optimized molecular machines based on light-driven rotary motion. Herein we demonstrate the thermal and photochemical rotational behavior of a series of third-generation light-driven molecular motors. The steric hindrance of the core unit exerted upon the rotors proved pivotal in controlling the speed of rotation, where a smaller size results in lower barriers. The presence of a pseudo-asymmetric carbon center provides the motor with unidirectionality. Tuning of the steric effects of the substituents at the bridgehead allows for the precise control of the direction of disrotary motion, illustrated by the design of two motors which show opposite rotation with respect to a methyl substituent. A third-generation molecular motor with the potential to be the fastest based on overcrowded alkenes to date was used to visualize the equal rate of rotation of both its rotor units. The autonomous rotational behavior perfectly followed the predicted model, setting the stage for more advanced motors for functional dynamic systems.
- Kistemaker, Jos C. M.,?tacko, Peter,Roke, Diederik,Wolters, Alexander T.,Heideman, G. Henrieke,Chang, Mu-Chieh,Van Der Meulen, Pieter,Visser, Johan,Otten, Edwin,Feringa, Ben L.
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supporting information
p. 9650 - 9661
(2017/07/24)
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- Hydrindene-1,3-dione compound catalysis synthetic method
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The present invention relates to a formula (II) shown hydrindene-1,3-dione compound catalysis synthetic method which is as follows: in an organic solvent and under a nitrogen atmosphere, in the presence of a catalyst, an oxidant, and an organic ligand and an adjuvant, self cyclization of a formula (I) compound is performed, the formula (II) compound is obtained by after-treatment after the end of the reaction, the method uses the new catalyst, the oxidant, the organic ligand, the organic solvent and the adjuvant for comprehensive selection and optimization to achieve material high-speed conversion, the yield of the target product can be greatly improved, the needs of industrial production can be better met, and the method has a broad market prospect.
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Paragraph 0045 - 0048
(2016/10/07)
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- Palladium-catalyzed chemoselective synthesis of indane-1,3-dione derivatives via tert-butyl isocyanide insertion
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A simple and efficient strategy for the synthesis of indane-1,3-dione derivatives through a palladium(0)-catalyzed reaction incorporating tert-butyl isocyanide has been developed. In addition, by applying this protocol as the key step, indenopyrazole derivatives can be easily synthesized in high yields in a one-pot procedure. This methodology is tolerant of a wide range of substrates and applicable to library synthesis.
- Duan, Huaqing,Chen, Zhong,Han, Li,Feng, Yulin,Zhu, Yongming,Yang, Shilin
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p. 6782 - 6788
(2015/06/25)
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- Design and synthesis of 4-benzyl-1-(2H)-phthalazinone derivatives as novel androgen receptor antagonists
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The androgen receptor (AR) plays important roles in multiple physiological functions, including differentiation, growth, and maintenance of male reproductive organs, and also has effects on hair and skin. In this paper, we report the synthesis of nonsteroidal AR antagonists having a 4-benzyl-1-(2H)-phthalazinone skeleton. Among the synthesized compounds, 11c with two ortho-substituents on the phenyl group potently inhibited SC-3 cell proliferation (IC50: 0.18 μM) and showed high wt AR-binding affinity (IC50: 10.9 μM), comparable to that of hydroxyflutamide (3). Compound 11c also inhibited proliferation of LNCaP cells containing T877A-mutated AR. Docking study of 11c with the AR ligand-binding domain indicated that the benzyl group is important for the antagonism. These phthalazinone derivatives may be useful for investigating potential clinical applications of AR antagonists.
- Inoue, Kazumi,Urushibara, Ko,Kanai, Misae,Yura, Kei,Fujii, Shinya,Ishigami-Yuasa, Mari,Hashimoto, Yuichi,Mori, Shuichi,Kawachi, Emiko,Matsumura, Mio,Hirano, Tomoya,Kagechika, Hiroyuki,Tanatani, Aya
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p. 310 - 319
(2015/09/01)
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- Palladium(ii)-catalyzed synthesis of functionalized indenones via oxidation and cyclization of 2-(2-arylethynylphenyl)acetonitriles
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A one-pot two-step synthesis of versatile indenones has been developed. This palladium(ii)-catalyzed transformation involves generation and condensation of ortho-functionalized 1,2-benzils from 2-(2-arylethynylphenyl)acetonitriles using Ph2SO as the oxidant. The resulting 3-cyanoindenones can be converted to various valuable molecules.
- Chen, Xuxing,He, Qian,Xie, Yuyuan,Yang, Chunhao
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p. 2582 - 2585
(2013/06/04)
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- Synthesis, characterization, antimicrobial activities and QSAR studies of some 10a-phenylbenzo[b]indeno[1,2-e][1,4]thiazin-11(10aH)-ones
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A series of 10a-phenylbenzo[b]indeno[1,2-e][1,4]thiazin-11(10aH)-ones (3) has been synthesized and tested for their antimicrobial activity. The antimicrobial evaluation data indicated that compounds, 3b, 3d, 3k and 3m exhibited very promising antibacterial activity and the compounds 3b and 3k exhibited notable activity, almost comparable to penicillin for Staphylococcus aureus and Bacillus subtilis respectively. The derivatives 3g and 3l exhibited high antifungal activity. Moreover, antibacterial activities were more prolific than antifungal activity. The QSAR studies indicated the importance of topological parameters, Kiers second order molecular index (κα 2) and molecular connectivity index (χ) in describing the antibacterial activity and electronic parameters, the energy of highest occupied molecular orbital (HOMO) and the dipole moment (μ) in describing the antifungal activity.
- Mor, Satbir,Pahal, Preeti,Narasimhan, Balasubramanian
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scheme or table
p. 176 - 189
(2012/07/31)
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- A novel prodrug strategy for β-dicarbonyl carbon acids: Syntheses and evaluation of the physicochemical characteristics of C-phosphoryloxymethyl (POM) and phosphoryloxymethyloxymethyl (POMOM) prodrug derivatives
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The C-phosphoryloxymethyl (POM) and phosphoryloxymethyloxymethyl (POMOM) prodrugs resulting from derivatization at the reactive α-carbon of β-dicarbonyl carbon acid drugs represent a unique approach for improving their chemical stability and aqueous solubility. This work evaluates the physicochemical and in vitro enzymatic bioconversion lability of selected prodrugs of phenylbutazone and phenindione. The POM and POMOM prodrug derivatives of phenylbutazone are highly water soluble (≥250 mg/mL), chemically stable with projected shelf-lives of 4.5 years (pH 3.5, 258C) and 1.1 years (pH 6.0, 25°C), respectively. Interestingly, both prodrug derivatives do not display a pH-dependency typical of many phosphate monoesters, although the similarities of their apparent thermodynamic activation parameters indicate a hydrolysis mechanism similar to other phosphates. These prodrugs undergo alkaline phosphatases catalyzed bioconversion to their respective carbon acids with an expected faster rate exhibited by the POMOM derivatives. Additionally, in marked contrast to the oxidative instability of phenindione, its POM prodrug is stable. The results from these studies reaffirm the rationale of transiently "masking" the reactive a-carbon/proton bond by covalently incorporating a POM or POMOM promoiety. This prodrug strategy presents a twofold advantage, enhancement of aqueous solubility and prevention of oxidative instability, two intrinsic formulation limitations found for β-dicarbonyl carbon acid drugs.
- Dhareshwar, Sundeep S.,Stella, Valentino J.
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experimental part
p. 2711 - 2723
(2011/04/15)
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- Chiral phosphoric acid catalyzed desymmetrization of meso-1,3diones: Asymmetric synthesis of chiral cyclohexenones
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Chiral effectiveness: The title transformation is applicable to a wide variety of substrates to give chiral cyclohexenones in high yields and with excellent enantioselecti vity (see scheme). To clarity the origin of the enantioselectivity ONIOM calculations were carried out
- Mori, Keiji,Katoh, Takuya,Suzuki, Tohru,Noji, Takuya,Yamanaka, Masahiro,Akiyama, Takahiko
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supporting information; experimental part
p. 9652 - 9654
(2010/04/28)
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- Synthesis of novel indane-1,3-dione derivatives and their biological evaluation as anticoagulant agents
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2-Substituted derivatives of indane-1,3-dione 3a-f , 5a-g, 6a-g were synthesized and investigated as anticoagulant agents. 2-Arylindane-1,3-diones (3) were obtained in the reaction of phthalide with appropriate arylaldehydes. 2-Arylmethyleneindane-1,3-diones (5) were prepared by condensation of indane-1,3-dione with the corresponding arylaldehydes. The compounds 5 were converted into their methyl analogues 6 by reduction with sodium tetrahydroborate. All of the compounds studied were screened for the anticoagulant activity. The highest prothrombin time was established for 2-[4-(methylsulfanyl) phenyl]indane-1,3-dione (3c) (PT = 33.71 (± 26.01) s), which was very close to PT of the drug anisindione (PT = 36.0 (± 26.42) s).
- Mitka, Katarzyna,Kowalski, Piotr,Pawelec, Dariusz,Majka, Zbigniew
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scheme or table
p. 613 - 618
(2010/04/05)
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- A facile three-component one-pot synthesis of structurally constrained tetrahydrofurans that are t-RNA synthetase inhibitor analogues
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A one-pot procedure for the efficient synthesis of tRNA inhibitor analogues was developed. Thus, three-component 1,3-dipolar cycloaddition reactions of carbonyl ylides derived from diazoindan-1,3-dione and aldehydes with other dipolarophiles in 1,1,2,2-tetrachloroethane in 80 °C gave ring-fused tetrahydrofurans having three stereocenters in good yield.
- Lu, Chong-Dao,Chen, Zhi-Yong,Liu, Hui,Hu, Wen-Hao,Mi, Ai-Qiao,Doyle, Michael P.
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p. 4856 - 4859
(2007/10/03)
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- Thermal cyclization of 3-azido-2-phenyl-indan-1-one to 5H-indeno[1,2-b]indol-10-one [1]
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3-Azido-2-phenylindan-1-one (4), which was obtained from 3-chloro-2-phenylindan-1-one (3), cyclizes on thermolysis to 5H-indeno[1,2-b]indol-10-one (5). Reaction of 3-azido-2-phenylindan-1-one (4) with triphenylphosphane gives 2-phenyl-3-(triphenylphosphoranylideneamino)-indan-1-one (6), which can be hydrolyzed to 3-amino-2-phenylindan-1-one (7). Attempts to perform a similar cyclization sequence with 3-chloro-2-pyridylindan-1-ones failed.
- Stadlbauer, Wolfgang,Fischer, Michaela
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p. 131 - 135
(2007/10/03)
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- Synthesis and pharmacological properties of sulfur derivatives of indane-1,3-dione
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Synthesis of sulfur derivatives of indane-1,3-dione, VIIb-c, VIIIa-b, IX and X is described. Results of a preliminary pharmacological screening of six compounds [VIIb, VIII, VIIIb, IX, X and XI] are presented.
- Mitka, Katarzyna,Kowalski, Piotr,Sulko, Jerzy,Wozniak, Marian,Kloc, Jowita,Chodkowska, Anna,Jagiello-Wojtowicz, Ewa
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p. 387 - 393
(2007/10/03)
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- Synthesis and nuclear magnetic resonance spectroscopy of indane structures: indanes mono- and disubstituted in the pentagonal ring
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Indanes monosubstituted and 1,2- and 1,3-disubstituted in the pentagonal ring were synthesized, and configurations were assigned to the 1,2-disubstituted compounds by means of nuclear magnetic resonance spectroscopy.Key words: mono- and disubstituted indanes, conformation, configuration, 1H and 13C NMR, synthesis.
- Alesso, Elba N.,Tombari, Dora G.,Ibanez, Adriana F.,Iglesias, Graciela Y. Moltrasio
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p. 1166 - 1170
(2007/10/02)
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- Rhodium(II) Acetate Catalysed Reactions of 2-Diazo-1,3-indandione and 2-Diazo-1-indanone with Various Substrates
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Decomposition of 2-diazo-1,3-indandione (3) by rhodium(II) acetate (1) in cyclohexane and in benzene results in overall carbon-hydrogen insertion to give 2-substituted 1,3-indandiones.Anisole, 1, and 3 yield 2-(4-methoxyphenyl)-1,3-indandione (74 percent); benzenes substituted by a single methyl or halogen groups yield the corresponding ortho- and para-substitution products.Spirocyclopropanes are obtained by rhodium(II)-catalyzed additions of 3 to olefins; electron-deficient olefins do not give adducts.Substituted 4H-indenofuran-4-ones and 2,3-disubstituted spiroindene>-1',3'-diones are formed from rhodium(II)-catalyzed reactions of 3 with acetylenes.Reactions of 1 and 3 with cyclohexane, olefins, acetylenes, and arenes involve selective electrophilic carbenic or ylidic processes. 2-Diazo-1-indanone (4) is converted by 1 to 2,2'-bis (48).Thiophenol reacts with 4 and 1 to yield 2-(phenylthio)-1-indanone (49).Cyclopropanations of cyclohexene and styrene by 4 as catalyzed by 1 result in spiroheptane-7,2'-indan>-1-one (50) and 2-phenylspiroinden>-1'(3'H)-one (51), respectively.
- Rosenfeld, M. J.,Shankar, B. K. Ravi,Shechter, H.
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p. 2699 - 2705
(2007/10/02)
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- Synthesis of 3-(4-Cyclopentene-1,3-dione-2-ylidene)-6-(diphenylmethylene)cyclohexadienes as Novel p-Quinodimethanes Stabilized by Antiaromaticity of Cyclopentadienone
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Title compounds, whose polarization is decreased by antiaromaticity of cyclopentadienone, have been synthesized through a novel Rh(II)-catalyzed arylation of cyclic 2-diazo-1,3-diones.
- Toda, Mitsuo,Hattori, Makiko,Okada, Keiji,Oda, Masaji
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p. 1263 - 1266
(2007/10/02)
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- An Unusual Synthesis of a Dihydrobenzanthrone
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The reaction of the aldehyde 1 with aluminium trichloride in benzene affords the dihydrobenzanthrone 2.The structure is confirmed by an X-ray analysis.Dehydrogenation of 2 yields the benzanthrone 3, which shows a greenish yellow fluorescence.According to the 1H-NMR and mass spectra, the deuterated products 5 and 6 are formed, when the key reaction is carried out in benzene.
- Veith, Reiner,Henke, Henning,Aldag, Reinhard,Braun, Manfred
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p. 265 - 268
(2007/10/02)
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- Reactions of Carbonyl Compounds in Basic Solutions. Part 9. Methoxide-catalysed Cyclization of Benzylidenephthalides and Methyl o-Phenylacetylbenzoates
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The detailed mechanism of the methoxide-catalysed rearrangement of substituted benzylidenephthalides and both normal and pseudo methyl o-phenylacetylbenzoates to form 2-phenylindane-1,3-diones has been studied.A rate-acidity function correlation for the reactions in methanolic dimethyl sulphoxide (DMSO) shows a linear increase in rate with increasing H- to reach a maximum in rate before decreasing, except for the p-nitro substrate.This derivative shows a rate decrease throughout the H- range.The ρ values in methanol and in 94 mol percent methanolic DMSO are 1.7 and -1.6, respectively.The kinetic isotope effect has been observed with kH/kD 0.8-1.0.The equilibrium constants for ring-chain tautomerism of the methyl o-phenylacetylbenzoates have been determined and shown to be independent of substituent and solvent composition.The rate-determining step is the intramolecular attack of the anion of the normal ester on the ester carbonyl group.In methanol and methanolic DMSO of high methanol content this is preceded by the ionization equilibrium of the normal ester.In methanolic DMSO of low methanol content and for the p-nitro substrate, the initial state is the anion itself.
- Bowden, Keith,Chehel-Amiran, Mohsen
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p. 2031 - 2034
(2007/10/02)
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- α,β-UNSATURATED THIO COMPOUNDS. XX. -CYCLOADDITION OF 3-AMINO-2-ARYL-1-INDENETHIONES TO NITRILIUM BETAINES AND PHENYL AZIDE
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N,N-Disubstituted 3-amino-2-aryl-1-indenethiones react with the N-oxides of aromatic nitriles or with benzonitrile phenylimine to form 5-spiroindene-substituted 1,4,2-oxathiazoles and 2-spiroindene-substituted 1,3,4-thiadiazolines.With phenyl azide only the transformation of the thiocarbonyl group into a phenylimine group occurs.In the reaction of N-unsubstituted aminoindenethione with benzonitrile N-oxide N,N-diacylation and the parallel transformation of the thione function into ketone function are observed.The reaction of 3-phenylamino-1-indenethione in the iminoenethiol form with benzonitrile N-oxide leads to the product from S-acylation and cycloaddition at the C=N bond with the formation of a 1,4,2-oxadiazoline ring.
- Korchevin, N. A.,Usov, V. A.,Voronkov, M. G.,Borodina, N. M.
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p. 1150 - 1154
(2007/10/02)
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- α,β-UNSATURATED THIO COMPOUNDS. XV. PROTONATION AND HYDROLYSIS OF 3-AMINO-2-CYCLOHEXENE-1-THIONES AND 3-AMINO-1-INDENETHIONES
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The protonation and acid hydrolysis of 3-amino-2-cyclohexene-1-thiones and 3-amino-1-indenethiones were investigated from the standpoint of the principle of hard and soft acids and bases.A relationship was established between the direction of hydrolysis of the thioketones and the nature of their protonation.
- Timokhina, L. V.,Usov, V. A.,Lavlinskaya, L. I.,Voronkov, M. G.
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p. 108 - 112
(2007/10/02)
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- Hypolipidemic Activity of Indan-1,3-dione Derivatives in Rodents
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A series of 2-substituted indan-1,3-dione derivatives, including alkyl (C-1-C-5), mono- and disubstituted phenyl, and other 2-aryl derivatives, were tested for hypolipidemic activity of CF1 male mice at 20 mg/kg per day.These derivatives reduced both serum cholesterol and triglycerides after 16 days of administration intraperitoneally. 2-(4-Methoxyphenyl)indan-1,3-dione was one of the more active compounds with 41percent reduction of serum cholesterol and 58percent reduction of serum triglyceride levels on day 16.This activity was confirmed in the rat after oral administration. 2-(2-Methylphenyl)- and 2-(4-chlorophenyl)indan-1,3-dione were effective in reducing serum triglyceride levels 58percent and 53percent, respectively, in mice.Serum cholesterol on day 16 was effectively reduced 46percent by 2-(2,4-dimethylphenyl)indan-1,3-dione.The indan-1,3-dione derivatives were more effective than clofibrate in lowering lipid levels in mice.A more detailed study on the effects of 2-(4-methoxyphenyl)indan-1,3-dione demonstrated that key enzymes in the de novo synthesis of lipids were inhibited by the drug lowering tissue levels of lipids but raising those in the feces.The alterations in lipid content of rat lipoprotein fractions by the drug appeared favorable.
- Murthy, A. R.,Wyrick, S. D.,Hall, I. H.
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p. 1591 - 1596
(2007/10/02)
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- SYNTHESIS AND PROPERTIES OF ESTERS OF 3-HYDROXY-2-PHENYLINDEN-1-ONE, 2-HYDROXYMETHYL-2-PHENYL-1,3-INDANEDIONE, AND CARBOXYLIC AND CARBONIC ACIDS
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The O-acylation of 2-phenyl-1,3-indanedione by carboxylic acid chlorides and chloroformates was realized in the presence of triethylamine.Growth-regulating activity was found in the obtained esters.The acylation of 2-hydroxymethyl-2-phenyl-1,3-indanedione by carboxylic acid chlorides was investigated in the presence of triethylamine.It was established that the reaction is unsuitable for the production of 2-acyloxymethyl-2-phenyl-1,3-indanediones.A method is proposed for the synthesis of these esters by the reaction of 2-iodomethyl-2-phenyl-1,3-indanedione with the potassium salts of carboxylic acids under the conditions of phase-transfer catalysis.
- Marshalkin, V. N.,Smirnova, T. V.
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p. 339 - 345
(2007/10/02)
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- INTERMEDIATES IN THE ELECTROLYTIC REDUCTION OF 2-PYRIDYL-1,3-INDANDIONES IN APROTIC MEDIA
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The character of the products of one-electron reduction of 2-pyridinia-1,3-indandiones (of the phthalone and ylid types) in aprotic media was studied by means of EPR spectroscopy.Free radicals with semidione structures are formed; their hfs constants are presented.Radicals with pyridinium structures are formed only under the condition of the presence of a strong electron acceptor (a cyano group) in the pyridinium ring of the molecule.The formation of unstable intermediates with dimeric structures is postulated as a result of studies by means of cyclical voltammetry.
- Benders, Yu. A.,Stradyn', Ya. P.,Baider, L. M.,Baumane, L. Kh.,Gavar, R. A.
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p. 193 - 200
(2007/10/02)
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- Synthesis of 1,2,3,9b-Tetrahydro-9b-hydroxy-1-phenylpyrroloisoindol-5-one via the Hydrazinolysis of 2-Phenyl-2-(2-phthalimidoethyl)indan-1,3-dione
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Hydrazinolysis of 2-phenyl-2-(2-phthalimidoethyl)indan-1,3-dione gave 1,2,3,9b-tetrahydro-9b-hydroxy-1-phenylpyrroloisoindol-5-one via the conversion of 2-(2-aminoethyl)-2-phenylindan-1,3-dione into the carbinolamine which underwent ring expansion followed by a transannular cyclisation.
- Crabb, Trevor A.,Patel, Ansuya,Newton, Roger F.,Price, Barry J.,Tucker, Michael J.
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p. 2783 - 2786
(2007/10/02)
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- Model Studies for a Molecular Mechanism of Action of Oral Anticoagulants
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Warfarin , a potent oral anticoagulant agent, is known to inhibit the enzyme vitamin K epoxide reductase.The molecular mechanism of inhibition, however, is not known.It is proposed that the two major classes of oral anticoagulants, the 3-substituted-4-hydroxycoumarins and the 2-substituted-1,3-indandiones, are mechanism-based inactivators of this enzyme.The proposed mechanism of inactivation involves enzyme-catalyzed activation of the oral anticoagulants by tautomerization to the hypothetically reactive diketo forms which then undergo attack by active-site nucleophiles.In order to test the chemistry of this proposal, it is shown that the two classes of oral anticoagulants are unreactive toward bases and nucleophiles (except for deprotonation), until they are electrophilically substituted at the 3-position of the coumarins or at the 2 position of the indandiones.These model compounds for the proposed enzyme-generated reactive intermediates, then, are shown to be highly reactive toward a variety of nucleophiles and support the hypothesis that the oral anticoagulants are converted by vitamin K epoxide reductase into reactive compounds which can acylate an active-site nucleophile and thereby inactivate the enzyme.
- Silverman, Richard B.
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p. 3910 - 3915
(2007/10/02)
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- The Acid-catalyzed Decomposition of α-Diazo β-Hydroxy Ketones
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The proton acid-catalyzed decomposition of 3-aryl-2-diazo-3-hydroxy-1-phenylpropanone (1) gave aryl and hydrogen migration products.The former was the enol-form (2) of 2-aryl-3-phenyl-1,3-propanedione and the latter was the enol- (3) and keto-form (4) of 1-aryl-3-phenyl-1,3-propanedione.The product ratios, 2/(3+4), were affected by the catalysts and solvents used.More polar solvents favored the formation of aryl migration products (2).On the other hand, the BF3-catalyzed decomposition of 1 gave acetylenic ketones as main products along with 2, 3, 4.The TsOH-catalyzed decomposition of 2-diazo-3-hydroxy-3-phenyl-1-indanone, (cyclic α-diazo β-hydroxy ketone), gave 2-phenyl-1,3-indandione quantitatively through phenyl migration.
- Miyauchi, Kazuo,Hori, Kimiaki,Hirai, Tsuguji,Takebayashi, Matsuji,Ibata, Toshikazu
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p. 2142 - 2146
(2007/10/02)
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- α,β-UNSATURATED THIO COMPOUNDS. XII. SYNTHESIS AND PROPERTIES OF S-ALKYL DERIVATIVES OF 3-AMINOINDENE-1-THIONES
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2-Substituted 3-amino-1-indenethiones are alkylated by alkyl iodides and triethyloxonium tetrafluoroborate with the formation of the corresponding salts of the S-alkyl derivatives or their bases.Hydrothiolysis, hydrolysis, and methanolysis of the N,N-disubstituted 3-alkylthio-2-arylindene-1-immonium salts lead to the production of new or little known types of organosulfur compounds.
- Korchevin, N. A.,Usov, V. A.,Oparina, L. A.,Dorofeev, I. A.,Tsetlin, Ya. S.,Voronkov, M. G.
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p. 1561 - 1566
(2007/10/02)
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