cas 606-23-5, 1,3-Indanedione | Articles data

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Access to Fluorenones Using Benzocyclopentynone Surrogate as Partner for the [2 + 2 + 2] Cycloaddition Reaction
A convenient and versatile procedure for the straightforward synthesis of substituted fluorenones as valuable scaffolds is described under rhodium catalysis. The present [2 + 2 + 2] cycloaddition reaction of diynes with 3-acetoxy or-3-alkoxyindenones as surrogates of the highly reactive benzocyclopentynone 2πpartner allows the preparation of various fluorenone-type derivatives in good yields and provides an additional and tunable process for the generation of more challenging molecules with application in pharmaceutical, polymer, and material sciences.
Manick, Anne-Doriane,Salgues, Bruno,Parrain, Jean-Luc,Zaborova, Elena,Fages, Frédéric,Amatore, Muriel,Commeiras, Laurent
p. 1894 - 1898
(2020)
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HCl-Catalyzed Aerobic Oxidation of Alkylarenes to Carbonyls
The construction of C?O bonds through C?H bond functionalization remains fundamentally challenging. Here, a practical chlorine radical-mediated aerobic oxidation of alkylarenes to carbonyls was developed. This protocol employed commercially available HCl as a hydrogen atom transfer (HAT) reagent and air as a sustainable oxidant. In addition, this process exhibited excellent functional group tolerance and a broad substrate scope without the requirement for external metal and oxidants. The mechanistic hypothesis was supported by radical trapping, 18O labeling, and control experiments.
Ding, Ling,Liu, Yuxiu,Niu, Kaikai,Shi, Xiaodi,Song, Hongjian,Wang, Qingmin
(2021/12/13)

(±)-Camphor sulfonic acid assisted IBX based oxidation of 1° and 2° alcohols
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Kumar, Kamlesh,Joshi, Penny,Rawat, Diwan S
(2021/09/02)

IBX-TfOH mediated oxidation of alcohols to aldehydes and ketones under mild reaction conditions
An efficient, practical and facile procedure has been developed for the oxidation of primary and secondary alcohols using IBX-TfOH catalytic system in 1,4-dioxane at ambient temperature. The reaction affords quantitative yields of the corresponding carbonyl compounds without the formation of over oxidized products. The present synthetic protocol is compatible with a variety of substrates having arene, heteroarene and alkene functionalities. The developed synthetic protocol can be used for higher scale reactions as evident by the oxidation of alcohol at 1 g scale in higher yields by a simple filtration process.
Kumar, Kamlesh,Kumar, Prashant,Joshi, Penny,Rawat, Diwan S
supporting information

(2020/03/04)

A supported manganese complex with amine-bis(phenol) ligand for catalytic benzylic C(sp3)-H bond oxidation
With regards to the importance of direct and selective activation of C-H bonds in oxidation processes, we develop a supported manganese amine bis(phenol) ligand complex as a novel catalyst with the aim of obtaining valuable products such as carboxylic acids and ketones that have an important role in life, industry and academic laboratories. We further analyzed and characterized the catalyst using the HRTEM, SEM, FTIR, TGA, VSM, XPS, XRD, AAS, and elemental analysis (CHN) techniques. Also, the catalytic evaluation of our system for direct oxidation of benzylic C-H bonds under solvent-free condition demonstrated that the heterogeneous form of our catalyst has high efficiency in comparison with homogeneous ones due to more stability of the supported complex. Furthermore, the structural and morphological stability of our efficient recyclable catalytic system has been investigated and all of the data proved that the complex was firmly anchored to the magnetite nanoparticles.
Karimpour, Touraj,Safaei, Elham,Karimi, Babak
p. 14343 - 14351
(2019/05/21)

Cyclopropanation of active methylene compounds with β-alkoxycarbonyl vinylsulfonium salts
An efficient synthesis of β-alkoxycarbonyl vinylsulfonium salts had been developed. Their reaction with indene-1,3-diones and other active methylene compounds provided cyclopropane carboxylates in good yields. A tentative reaction mechanism was proposed.
Guo, Shenquan,Zhang, Niuniu,Tang, Xiangzheng,Mao, Zhifeng,Zhang, Xuejing,Yan, Ming,Xuan, Yining
supporting information
p. 406 - 408
(2018/09/25)

A Method for Synthesis of 3-Hydroxy-1-indanones via Cu-Catalyzed Intramolecular Annulation Reactions
We report a facile and highly efficient method that copper-catalyzed intramolecular annulation to synthesize 3-hydroxy-1-indanones employing simple 2-ethynylbenzaldehyde as starting materials was achieved successfully. This protocol provided a simple synthetic approach to afford 3-hydroxy-1-indanones under mild conditions in good to excellent yields.
He, Guoxue,Wu, Chenglin,Zhou, Jianhui,Yang, Qiaolan,Zhang, Chunmei,Zhou, Yu,Zhang, Huabei,Liu, Hong
p. 13356 - 13362
(2018/11/20)

Generation and Confinement of Long-Lived N-Oxyl Radical and Its Photocatalysis
Generation of controllable carbon radical under the assistance of N-oxyl radical is an efficient method for the activation of C-H bonds in hydrocarbons. We herein report that irradiation of α-Fe2O3 and N-hydroxyphthalimide (NHPI) under 455 nm light generates phthalimide-N-oxyl radical (PINO), which after being formed by oxidation with holes, is confined on α-Fe2O3 surface. The half-life time of the confined radical reaches 22 s as measured by in situ electron paramagnetic resonance (EPR) after the light being turned off. This allows the long-lived N-oxyl radical to abstract the H from C-H bond to form a carbon radical that reacts with molecular oxygen to form R3C-OO· species, decomposition of which leads to oxygenated products.
Zhang, Chaofeng,Huang, Zhipeng,Lu, Jianmin,Luo, Nengchao,Wang, Feng
p. 2032 - 2035
(2018/02/19)

1. 3 - Indandione synthesis process
The invention belongs to the technical field of synthesis of pharmaceutical intermediates, in particular to a 1, 3 - indandione synthesis process, comprising the following steps: step 1, the phthalic acid dimethyl and ethyl acetate added in a reaction vessel, opening the stirring, adding sodium methoxide, heating to 40 - 50 °C to stop heating; step 2, continuing to stir the reaction, to the reaction system is yellow clotting bipeltate, added ethyl acetate, keep the reaction system at a temperature of 70 - 80 °C reaction under the condition of the 3 - 4 hours, cooling to 20 °C following, filtering, the filter cake washing with ethyl acetate, drying, to obtain the intermediate; step 3, taking the step 1 intermediate prepared added in a reaction vessel, the concentrated hydrochloric acid is mixed with water added in a reaction vessel after, opening stirring, heated to 45 - 55 °C, thermal insulation reaction until there is no air bubble generation; lowering the temperature to 20 °C following, filtered, the filter cake washing with ethyl acetate, collecting filter cake, vacuum drying, to obtain the product of 1, 3 - indandione; the synthesis technique is simple, mild condition, and the yield is high.
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Paragraph 0022-0025; 0026; 0027

(2018/08/28)

Method for directly oxidizing benzyl-position C-H bond into ketone
The invention discloses a method for directly oxidizing a benzyl-position C-H bond into ketone, wherein aryl ethyl compounds are catalyzed and oxidized by nitrite ester; a synergistic catalytic system of free radical initiator and nitrite ester is adopted, and a catalytic system of non-metallic catalyst and oxygen is adopted, the oxidization of the C-H bond of a free radical-activated aryl side chain is simple in operation; after completing the reaction, petroleum ether/ethyl acetate at a volume ratio of (50-1):1 is used as an eluent; column chromatography separation is performed to obtain a target product. The catalytic system in the invention uses oxygen as an oxygen source and has high atomic economy; the invention is a non-metallic catalytic system and provides a novel method for avoid metal residues in synthetic drugs; for diethyl aromatic hydrocarbon, the method provided by the invention can be adopted to selectively oxidize diethyl aromatic hydrocarbon into monoketone and diketone; the method of the invention can be adopted to efficiently synthesize tranquillizer lenperone, so that a novel method for synthesizing lenperone is provided.
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Paragraph 0102; 0103; 0106; 0107

(2017/08/29)

Organopromoted Selectivity-Switchable Synthesis of Polyketones
In this work, an organopromoted metal-free pharmaceutical-oriented selectivity-switchable benzylic oxidation was developed, affording mono-, di-, and trioxygenation products, respectively, using oxygen as the oxidant under mild conditions. This process facilitates dioxygenation of 2,6-benzylic positions of heterocycles, which could be inhibited by heterocycle chelation to the metal cocatalysts. Enantiopure chiral ketones could also be prepared. The noninvolvement of transition metals and toxins avoids metal or hazardous residues, consequently ensuring a final-stage gram-scale synthesis of Lenperone.
Liu, Jie,Hu, Kang-Fei,Qu, Jian-Ping,Kang, Yan-Biao
supporting information
p. 5593 - 5596
(2017/10/25)

Regioselective Synthesis, Antimicrobial Evaluation and QSAR Studies of Some 3-Aryl-1-heteroarylindeno[1,2-c]pyrazol-4(1H)-ones
A series of seventeen 3-aryl-1-heteroarylindeno[1,2-c]pyrazol-4(1H)-ones (4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m, 4n, 4o, 4p, 4q) has been synthesized and characterized by spectral (IR, 1H NMR, and mass), X-ray crystallography and analytical results. All the indenopyrazoles (4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m, 4n, 4o, 4p, 4q) were tested for their in vitro antimicrobial activity against two Gram-positive bacteria viz. Bacillus subtilis (MTCC 441) and Staphylococcus aureus (MTCC 7443), two Gram-negative bacteria, viz. Escherichia coli (MTCC 42) and Pseudomonas aeruginosa (MTCC 741) and two fungi, viz. Candida albicans (MTCC 183) and Aspergillus niger (MTCC 282) using ceftriaxone and fluconazole as standard references against bacterial and fungal strains, respectively. Among the synthesized derivatives, 4f against B. subtilis and S. aureus, 4e against E. coli, 4g and 4j against P. aeruginosa, 4k and 4l against C. albicans, and 4k against A. niger were found to exhibit appreciable antimicrobial activities. However, 4g (minimum inhibitory concentration, 0.0036 μmol/mL) was found to be more potent than the reference, that is, fluconazole (minimum inhibitory concentration, 0.0050 μmol/mL) against A. niger. Moreover, both antibacterial and antifungal activities were found to be prolific. The radial distribution function parameters were found to be important for description of activities against the modeled strains in quantitative structure–activity relationship studies.
Mor, Satbir,Mohil, Rajni,Nagoria, Savita,Kumar, Ashwani,Lal, Kashmiri,Kumar, Devinder,Singh, Virender
p. 1327 - 1341
(2017/03/27)

MIL-101 as reusable solid catalyst for autoxidation of benzylic hydrocarbons in the absence of additional oxidizing reagents
Materiaux de l'Institute Lavosier-101 (MIL-101) promotes benzylic oxidation of hydrocarbons exclusively by molecular oxygen in the absence of any other oxidizing reagent or initiator. Using indane as model compound, the selectivity toward the wanted ol/one mixture is higher for MIL-101(Cr) (87% selectivity at 30% conversion) than for MIL-101(Fe) (71% selectivity at 30% conversion), a fact that was associated with the preferential adsorption of indane within the pore system. Product distribution and quenching experiments with 2,2,6,6-tetramethyl-1-piperidinyloxy, benzoic acid, and dimethylformamide show that the reaction mechanism is a radical chain autoxidation of the benzylic positions by molecular oxygen, and the differences in selectivity have been attributed to the occurrence of the autoxidation process inside or outside the metal organic framework pores. MIL-101 is reusable, does not leach metals to the solution, and maintains the crystal structure during the reaction. The scope of the benzylic oxidation was expanded to other benzylic compounds including ethylbenzene, n-butylbenzene, iso-butylbenzene, 1-bromo-4-butylbenzene, sec-butylbenzene, and cumene.
Santiago-Portillo, Andrea,Navalón, Sergio,Cirujano, Francisco G.,Xamena, Francesc X. Llabrés I,Alvaro, Mercedes,Garcia, Hermenegildo
p. 3216 - 3224
(2015/06/16)

Palladium-catalyzed chemoselective synthesis of indane-1,3-dione derivatives via tert-butyl isocyanide insertion
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
p. 6782 - 6788
(2015/06/25)

Rapid synthesis of isoquinolinones by intramolecular coupling of amides and ketones
Amides and ketones were intramolecularly coupled in the presence of KOt-Bu/DMF. The reaction provided good yields of a variety of isoquinolinones. A reaction mechanism of radical addition and subsequent E2-elimination is proposed.
Wei, Wen-Tao,Liu, Yu,Ye, Lin-Miao,Lei, Rong-Hui,Zhang, Xue-Jing,Yan, Ming
supporting information
p. 817 - 824
(2015/02/19)

Highly Efficient Oxidation of Secondary Alcohols to Ketones Catalyzed by Manganese Complexes of N4 Ligands with H2O2
The manganese complex Mn(S-PMB)(CF3SO3)2 was proven to be highly efficient in the catalytic oxidation of several benzylic and aliphatic secondary alcohols with H2O2 as the oxidant and acetic acid as the additive. A maximum turnover number of 4700 was achieved in the alcohol oxidation. In addition, the Hammett analysis unveiled the electrophilic nature of this manganese catalyst with N4 ligand. (Chemical Equation Presented).
Shen, Duyi,Miao, Chengxia,Xu, Daqian,Xia, Chungu,Sun, Wei
supporting information
p. 54 - 57
(2015/07/28)

Ethenolate transfer reactions: A facile synthesis of vinyl esters
A simple and efficient metal-free ethenolate transfer reaction has been elaborated in moderate-to-high yields from vinyl acetate. This reaction was accomplished by generation of potassium ethenolate, which was then reacted with homo and mixed anhydrides of aliphatic, aryl and heteroaryl acids, to yield the corresponding vinyl esters. The utility of thus generated vinyl esters was then probed by carrying out intramolecular Heck reactions to give isobenzofuran-1(3H)-one derivatives in excellent yields. Copyright
Appaye, Srinivasan Kaliyaperumal,Nikumbh, Satish Pandurang,Govindapur, Rajeshwar Reddy,Banerjee, Shyamapada,Bhalerao, Dinesh S.,Kumar, Unniaran K. Syam
p. 1115 - 1122
(2014/09/17)

Asymmetrie synthesis of bicyclic diol derivatives through metal and enzyme catalysis: Application to the formal synthesis of sertraline
Enzyme- and ruthenium-catalyzed dynamic kinetic asymmetric transformation (DYKAT) of bicyclic diols to their diacetates was highly enantio- and diastereoselective to give the corresponding diacetates in high yield with high enantioselectivity (99.9% ee). The enantiomerically pure diols are accessible by simple hydrolysis (NaOH, MeOH), but an alternative enzyme-catalyzed ester cleavage was also used to give the trans-diol (R,R)1b in extremely high diastereomeric purity (trans/cis = 99.9:0.1, >99.9% ee). It was demonstrated that the diols can be selectively oxidized to the ketoalcohols in a ruthenium-catalyzed Oppenauer-type reaction. A formal enantioselective synthesis of sertraline from a simple racemic cis/trans diol 1b was demonstrated.
Krumlinde, Patrik,Bogar, Krisztian,Baeckvall, Jan-E.
scheme or table
p. 4031 - 4036
(2010/08/05)

Synthesis and biological evaluation of some hydrazones and carbazones of indane-l,3-dione
Diethyl phthalate on treatment with ethyl acetate in sodium ethoxide gives sodium salt of ester derivative, which on neutralization in presence of sulphuric acid affords indane-1,3-dione 1. Various hydrazines and carbazides on condensation with 1 in ethanol under reflux furnish the corresponding hydrazones and carbazones 2a-g. The structures of the compounds have been established by IR and 'H NMR spectral data. All the synthesized compounds have been evaluated for their anticoagulant and antimicrobial activities. Among these, compounds 2b and 2c have shown significant anticoagulant activity. All the compounds exhibited mild to moderate antimicrobial activities. Among these compounds 2a and 2g are found to have antimicrobial activities comparable to that of standard drugs used.
Jubie,Meenab,Ramaseshu,Jawahar,Vijayakumar
scheme or table
p. 1261 - 1263
(2010/12/25)

Efficient near infrared D-π-A sensitizers with lateral anchoring group for dye-sensitized solar cells
A new strategy in which the anchoring group is separated from the acceptor groups of the dyes was developed; among these dyes, the HY103 dye gives a maximum IPCE value of 86% at 660 nm and an η value of 3.7% in the NIR region reported in DSCs.
Hao, Yan,Yang, Xichuan,Cong, Jiayan,Tian, Haining,Hagfeldt, Anders,Sun, Licheng
supporting information; scheme or table
p. 4031 - 4033
(2009/12/09)

Aqueous phase C-H bond oxidation reaction of arylalkanes catalyzed by a water-soluble cationic Ru(III) complex [(pymox-Me2) 2RuCl2]+BF4-
The cationic complex [(pymox-Me2)RuCl2] -BF4- was found to be a highly effective catalyst for the C-H bond oxidation reaction of arylalkanes in water. For example, the treatment of ethylbenzene (1.0 mmol) with t-BuOOH (3.0 mmol) and 1.0 mol % of the Ru catalyst in water (3 mL) cleanly produced PhCOCH3 at room temperature. Both a large kinetic isotope effect (kH/k D) 14) and a relatively large Hammett value (ρ) -1.1) suggest a solvent-caged oxygen rebounding mechanism via a Ru(IV)-oxo intermediate species.
Yi, Chae S.,Kwon, Ki-Hyeok,Lee, Do W.
supporting information; experimental part
p. 1567 - 1569
(2009/08/07)

Enamino derivatives of 1,3-dioxoindane-2-carboxylic acid
(Chemical Equation Presented) Although 1,3-dioxoindane-2-carboxylic acid is highly unstable, its enamino derivatives can be isolated by careful hydrolysis of their esters with 2,4-dihydroxy-1,4-naphthoquinone. Crystal structure determination reveals the formation of two intramolecular hydrogen bonds, offering thus a possible explanation for the stability of these acids.
Malamidou-Xenikaki, Elizabeth,Spyroudis, Spyros,Tsanakopoulou, Maria,Krautscheid, Harald
experimental part
p. 8392 - 8397
(2009/04/11)

Product selection through photon flux: Laser-specific lactone synthesis
(Chemical Equation Presented) Lasers flux their muscles: The Norrish type I and type II reactions of 1,3-indandiones can be controlled by judicious choice of light source. Selectivity depends on photon flux, not wavelength. Laser irradiation lead to lacto
Roscini, Claudio,Davies, David M. E.,Berry, Malcolm,Orr-Ewing, Andrew J.,Booker-Milburn, Kevin I.
experimental part
p. 2283 - 2286
(2009/02/08)

Aerobic oxidative kinetic resolution of racemic alcohols with bidentate ligand-binding Ru(salen) complex as catalyst
Chiral Ru(salen)(nitrosyl) complex 1 is a useful catalyst for asymmetric aerobic oxidation of alcohols under photo-irradiation. In?this study, it was found that addition of β-hydroxy ketone or 1,3-diketone had a significant influence on its asymmetric catalysis. For example, the addition of 1,3-bis(p-bromophenyl)propane-1,3-dione 9 improved the relative reaction ratio in kinetic resolution of simple racemic secondary alcohols up to 30, while the addition gave an adverse effect on desymmetrization of an acyclic meso-1,3-diol. This additive effect was considered to be attributable to the chelate formation of the β-hydroxy ketone or 1,3-diketone with a Ru(salen) complex.
Nakamura, Yukie,Egami, Hiromichi,Matsumoto, Kazuhiro,Uchida, Tatsuya,Katsuki, Tsutomu
p. 6383 - 6387
(2008/02/05)

Effective oxidation of benzylic and aliphatic alcohols with hydrogen peroxide catalyzed by a manganese(III) Schiff-base complex under solvent-free conditions
A variety of alcohols were oxidized efficiently into the corresponding ketones and carboxylic acids in excellent yields with hydrogen peroxide using a manganese(III) Schiff-base complex as a catalyst under solvent-free and mild conditions. The oxidation procedure is very simple and the products are easily isolated in excellent yields.
Mardani, Hamid R.,Golchoubian, Hamid
p. 2349 - 2352
(2007/10/03)

Synthesis of 2-(aryl methylene)-(1H)-indane-1,3-(2H)-diones as potential fungicidal and bactericidal agents
Reaction of diethyl phthalate 1 and ethyl acetate 2 in the presence of sodium metal and ethanol affords indane-1, 3-dione 3, which have been substituted at C-2 position with different aromatic aldehydes 4, to yield their respective aryl derivatives of indane-1,3-dione 5a-h. These derivatives are evaluated for their antifungal and antibacterial activity. The structures of all the compounds are determined by IR, 1H NMR and mass spectrometry.
Meena,Shankar,Ramseshu,Giles,Prakash,Venkataraman
p. 1572 - 1575
(2007/10/03)

ARYLINDENOPYRIDINES AND RELATED THERAPEUTIC AND PROPHYLACTIC METHODS
This invention provides novel arylindenopyridines of the formula: and pharmaceutical compositions comprising same, useful for treating disorders ameliorated by antagonizing Adensine A2a receptors or reducing PDE activity in appropriate cells. This invention also provides therapeutic and prophylactic methods using the instant pharmaceutical compositions.
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(2008/06/13)

Arylindenopyridines and related therapeutic and prophylactic methods
This invention provides novel arylindenopyridines of the formula: and pharmaceutical compositions comprising same, useful for treating disorders ameliorated by antagonizing Adensine A2a receptors or reducing PDE activity in appropriate cells. This invention also provides therapeutic and prophylactic methods using the instant pharmaceutical compositions.
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(2008/06/13)

Arylindenopyridines and related therapeutic and prophylactic methods
This invention provides novel arylindenopyridines of the formula: , and pharmaceutical compositions comprising same, useful for treating disorders ameliorated by reducing PDE activity in appropriate cells. This invention also provides therapeutic and prophylactic methods using the instant pharmaceutical compositions.
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(2008/06/13)

Indanone herbicide compositions and use thereof
This invention relates to an indanone herbicidal composition comprising a compound having the general formula wherein Y is an oxygen atom or a hydrazono group, R is alkyl or substituted alkyl, X is a hydrogen atom or is one to three substituents independently selected from the group consisting of halo, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, phenyl, phenalkyl, phenalkenyl, phenalkynyl, cyano, haloalkoxy, 1,3-dioxalan-2-yl, hydroxyimino and nitro, and an agronomically acceptable carrier. The invention also discloses a method of use of these compositions.
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(2008/06/13)

Synthesis, structure, and nucleophile-induced rearrangements of spiroketones
Three tetraketones based on the 2,2'-spirobiindan-1,1',3,3'-tetraone skeleton were prepared and investigated. All three compounds show spiroconjugation between their perpendicular π-networks. The interaction results in lowering of the energy of the LUMO of the systems by ca. 0.2-0.3 eV as compared to non-spiroconjugated models. The spiroketones are susceptible to nucleophile-induced retro-Claisen condensations that lead to molecular rearrangements destroying spiro connectivity.
Maslak, Przemyslaw,Varadarajan, Sridhar,Burkey, Jeffrey D.
p. 8201 - 8209
(2007/10/03)

Use of benzotrifluoride as solvent for chromium-catalysed oxidations with sodium percarbonate
Chromium(VI)-catalysed oxidations of alcohols and benzylic methylene groups by sodium percarbonate have been carried out in refluxing benzotrifluoride; comparisons with previous studies showed that this solvent is a valuable alternative to 1,2-dichloroethane for such reactions.
Delaval, Nicolas,Bouquillon, Sandrine,Henin, Francoise,Muzart, Jacques
p. 286 - 287
(2007/10/03)

Indanone herbicide compositions and use thereof
This invention relates to an indanone herbicidal composition comprising a compound having the general formula wherein Y is an oxygen atom or a hydrazono group, R is alkyl or substituted alkyl, X is a hydrogen atom or is one to three substituents independently selected from the group consisting of halo, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, phenyl, phenalkyl, phenalkenyl, phenalkynyl, cyano, haloalkoxy, 1,3-dioxalan-2-yl, hydroxyimino and nitro, and an agronomically acceptable carrier. The invention also discloses a method of use of these compositions.
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(2008/06/13)

Synthesis and Study of Heterocyclic Compounds Derived from Indane-1,3-dione
N,N′-Bis(1-oxoinden-3-yl)-1,3,4-thiadiazole-2,5-diamine and its benzoyl derivative N,N′-bis-(3-benzoyloxyinden-1-ylidene)-1,3,4-thiadiazole-2,5-diamine. The benzoyl derivative has reduced melting point and is better soluble in organic solvents.
Berezina,Vorob'ev,Smirnov
p. 968 - 971
(2007/10/03)

Chromium-Mediated Benzylic Oxidations by Sodium Percarbonate in the Presence of a Phase Transfer Catalyst.
In the presence of catalytic amounts of (n-Bu3SnO)2CrO2, Adogen 464 and p-toluenesulfonic acid, benzylic methylene groups are effectively oxidized into alcohols and ketones by sodium percarbonate in refluxing acetonitrile.
Muzart, Jacques,Aiet-Mohand, Samia
p. 5735 - 5736
(2007/10/02)

Phenyliodoniophenolates from 1,3-Dihydroxybenzene Derivatives
A new type of phenyliodonio phenolates resulting from the reaction of 1,3-dihydroxy benzene derivatives and (diacetoxyiodo)benzene were isolated and characterized.The new phenolates afforded cyclization products from their photochemical reaction with alkenes and alkynes and phenyl ethers from their thermal rearrangement.A possible reaction pathway is proposed in order to explain the regioselectivity of these reactions.
Spyroudis, Spyros,Tarantili, Petroula
p. 11541 - 11552
(2007/10/02)

Proton transfer from carbon acids to carbanions. 1. Reactions of various carbon acids with the anions of substituted benzylmalononitriles in 90% Me2SO-10% water. determination of intrinsic barriers of identity reactions from the marcus relationship
A kinetic study of the reversible deprotonation of 9-cyanofluorene (2), 1,3-indandione (3), 4-nitrophenyl-acetonitrile (4), (3-nitrophenyl)nitromethane (5), and (4-nitrophenyl)nitromethane (6) by the anions of substituted benzylmalononitrile (1-X-) in 90% Me2SO-10% water (v/v) at 20 °C is reported. Intrinsic rate constants and intrinsic barriers of these reactions have been determined by extrapolation or interpolation of Br?nsted plots whose slopes (β) are all close to 0.5. Intrinsic barriers of the identity reactions CH + C- ? C- + CH (CH = 2,3,4,and phenylnitromethane) have been estimated on the basis of the Marcus equation, coupled with either a plausible value for the identity barrier of the reaction AH+ + A ? A + AH+ (A = piperidine or morpholine) ("amine method") or a plausible value for the identity barrier of the reaction 2 + 2- ? 2- + 2 ("9-cyanofluorene method"). There are discrepancies in the identity barriers for CH + C- ? C- + CH (CH = 2, 3, 4, and phenylnitromethane) calculated by the two methods. Possible reasons for these discrepancies and the significance of the results in terms of the validity and scope of the Marcus equation are discussed.
Bernasconi, Claude F.,Ni, Jiu Xiang
p. 5060 - 5066
(2007/10/02)

Acylation of Aroyl Chlorides via a Template Friedel-Crafts Process: Synthesis of Indan-1,3-diones
Variously substituted indan-1,3-diones have been regioselectively prepared in a one-pot synthesis by sequential cross-condensation-cycloacylation of aromatic acyl chlorides and acetyl chloride or malonyl dichloride, electrophilic acylation of aromatic acyl chlorides representing the key step in the process.The synergism of the aromatic carbonyl enolization and the organization of the reacting system promoted by the metal is emphasized to account for the mild reaction conditions.
Sartori, Giovanni,Bigi, Franca,Maggi, Raimondo,Baraldi, Davide,Casnati, Giuseppe
p. 2985 - 2988
(2007/10/02)

Synthesis of 1,3-Diketones Using α-Diazo Ketones and Aldehydes in the Presence of Tin(II) Chloride
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Padwa, Albert,Hornbuckle, Susan F.,Zhang, Zhijia,Zhi, Lin
p. 5297 - 5299
(2007/10/02)

Derivatives of 1,4-Naphthoquinone via 3-(Phenyliodonio)-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide
The title compound 3 reacts with various electrophiles such as hydrogen halides, benzoyl chloride, iodomethane, and bromine to afford 3-halo derivatives of 2-hydroxy-1,4-naphthoquinone. 3 reacts also with dimethyl sulfide to give a trans-ylidation product; photochemically, furan derivatives are formed with 2-methyl-2-butene, styrene, and phenylacetylene.Carbon disulfide affords the 2-thioxo-1,3-oxathiole derivative 15.
Hatzigrigoriou, Evangelia,Spyroudis, Spyros,Varvoglis, Anastasios
p. 167 - 170
(2007/10/02)

Nucleophilic Addition to Olefins. 13. Kinetics of Hydrolysis of Benzylidene-1,3-indandione
A complex kinetic analysis of the four-step hydrolysis of benzylidene-1,3-indandione into benzaldehyde and 1,3-indandione in 50percent Me2SO-50percent water is reported.The four steps (see Scheme 1) are (1) nucleophilic addition of hydroxide ion or water to form the adduct TOH(1-), (2) carbon protonation of TOH(1-) to form TOH0, (3) oxygen deprotonation of TOH0 to form TO(1-), and (4) breakdown of TO(1-) into benzaldehyde and 1,3-indandione or its anion.There is also a direct water-catalyzed pathway from TOH0 to benzaldehyde and 1,3-indandione.Rate and equilibrium constants of the various steps are compared with analogous parameters in the hydrolysis of benzylidenemalononitrile, β-nitrostyrene, benzylidene Meldrum's acid, and 1,1-dinitro-2,2-diphenylethylene.The following conclusions emerge. (1) The equilibrium constants of the carbanion-forming steps (step 1 forward, step 2 reverse, step 4 forward) correlate fairly well with the pKa values of the corresponding parent carbon acids 1,3-indandione, malononitrile, nitromethane, Meldrum's acid, and 1,1-dinitroethane, although steric as well as other factors make the correlations less than perfect. (2) The intrinsic rate constants (k for K=1) for the carbanion-forming steps (step 1 with OH(1-), and step 4) decrease with increasing resonance stabilization of the carbanion, just as is the case for the deprotonation of the corresponding parent carbon acids.However, the effect of the activating substituent(s) on the intrinsic rates of these steps is only about half (on a logarithmic scale) as large as for the proton transfer. (3) The effect of the activating substituent(s) on the intrinsic rates of water addition to the olefin, and of the direct water-catalyzed breakdown of TOH0 to products, is significantly smaller than for step 1 (OH(1-) attack) and k4, and in some cases even reversed, with the intrinsic rate being higher for the system with substituents capable of strong resonance.This is attributed to a special transition-state stabilization by internal hydrogen bonding from the water to the oxygen anion in these water-catalyzed reactions.
Bernasconi, Claude F.,Laibelman, Alan,Zitomer, Janie L.
p. 6563 - 6570
(2007/10/02)

Unusual and Competitive Side Reactions during C-Alkylation of Indan-1,3-dione
Direct C-alkylation of indan-1,3-dione (I) with reactive alkyl halides under mild conditions leads to the formation of 2-alkyl-indan-1,3-dione (II) along with bis-alkylated derivative (III) and traces of 2-alkylated bindone (a self-condensation of indan-1,3-dione).The isolation and characterisation of these compounds are described.
Padmanabhan, P. V.,Ramana, D. V,Ramadas, S. R.
p. 1 - 4
(2007/10/02)

EXTREMELY REACTIVE CARBON-CARBON DOUBLE BONDS-I; REACTIONS WITH 2-(9-XANTHYLIDENE)-, 2-(9-THIOXANTHYLIDENE)-, AND 2-(9-FLUORENYLIDENE)-INDANE-1,3-DIONE. A CONTRIBUTION ON THE STRUCTURE AND REACTIVITY OF NON-PLANAR C-C DOUBLE BONDS
The compounds in the title (cf 1a, 1b and 2) react with various reagents, often under mild conditions, mostly by breaking of the central double bond.According to X-ray diffraction the central double bond of 2-(9-xanthylidene)indane-1,3-dione is inclined by 47.2 deg.The relationship between the structure and reactivity of the compounds in the title is discussed.
Schoenberg, Alexander,Singer, Erich,Stephan, Werner,Sheldrick, William S.
p. 2429 - 2438
(2007/10/02)

FLASH-THERMOLYSIS OF METHYLENEPHTALIDE AND 3-METHYLENE-2-COUMARANONE
The synthesis and flash-thermolysis of methylenephtalide 1 and 3-methylene-2-coumaranone 2 are reported.At high temperatures ( 1000 deg C) these two isomeric lactones do not extrude CO2 but give rise to new clean thermal rearrangements.
Bloch, R.,Orvane, P.
p. 3597 - 3600
(2007/10/02)