- 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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- New donor-acceptor stenhouse adducts as visible and near infrared light polymerization photoinitiators
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Polymerization photoinitiators that can be activated under low light intensity and in the visible range are being pursued by both the academic and industrial communities. To efficiently harvest light and initiate a polymerization process, dyes with high molar extinction coefficients in the visible range are ideal candidates. In this field, Donor-acceptor Stenhouse Adducts (DASA) which belong to a class of recently discovered organic photochromic molecules still lack practical applications. In this work, a series of DASA-based dyes are proposed as photoinitiators for the free radical polymerization of (meth)acrylates upon exposure to a near infrared light (laser diode at 785 nm).
- Bonardi, Aude-Héloise,Dumur, Frédéric,Duval, Sylvain,Gigmes, Didier,Lalevée, Jacques,Noirbent, Guillaume,Xu, Yangyang
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supporting information
(2020/05/28)
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- Some Reactions with Indane-1,3-dione: A Facile Synthesis of Pentacycline Heterocyclic Analogues
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Indane-1,3-dione 1 reacts with salicylaldehyde 5 and malononitrile 3 to afford 6-amino-7-imino-7H-indeno-[2′,1′:5,6]-pyrano-[3,4-c]-chromene 6, which could be transformed into the corresponding 7-oxo derivative 7. 2-(3-Oxoindan-1-ylidene)-malononitrile 10 couples with the diazonium salts 8, 14, and 15 to afford after cyclization the indeno-[2,1-c]-pyridazine 13 and the indeno-[2′,1′:3,4]-pyridazino-[1,6-a]-quinazoline derivatives 20 and 21, respectively.
- Abdelrazek, Fathy M.,Metz, Peter,Jaeger, Anne
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- Synthesis of Functionalized Indenones via Rh-Catalyzed C-H Activation Cascade Reaction
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An efficient and expeditious protocol for the synthesis of diverse difunctionalized indenones through rhodium-catalyzed C-H activation and multistep cascade reaction of benzimidates and alkenes has been developed. The transformation involves the cleavage and formation of multiple bonds in one pot under mild reaction conditions, and Mn(OAc)2 plays an important role in the reaction.
- Lv, Ningning,Chen, Zhengkai,Liu, Yue,Liu, Zhanxiang,Zhang, Yuhong
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p. 2588 - 2591
(2017/05/24)
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- Syntheses, Structures and Optoelectronic Properties of Spiroconjugated Cyclic Ketones
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Synthetic investigations towards spiroconjugated ketones and derivatives thereof are presented. These studies led to the development of a short procedure for the synthesis of spiroconjugated tetraketone 1 in two steps with 10 % overall yield and the first-time synthesis of spirocyclic trindone 2. The optoelectronic properties of these compounds based on spectroscopic and electrochemical measurements in combination with DFT calculations as well as their molecular structures in the solid state are presented and discussed.
- Wilbuer, Jennifer,Schnakenburg, Gregor,Esser, Birgit
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p. 2404 - 2412
(2016/06/01)
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- A selective solvent-free self-condensation of carbonyl compounds utilizing microwave irradiation
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An environmentally benign microwave-assisted solvent-free self-condensation of carbonyl compounds was developed using catalytic amounts of triethylamine and lithium perchlorate. Changing the amount of lithium perchlorate helps in controlling the ratio of the single-condensation and double-condensation products. The effect of other additives and microwave activation was also investigated. The optimized conditions were then applied to various cyclic/acyclic ketones and aldehydes, with selectivity observed in many cases.
- Sharma, Lalit Kumar,Kim, Kyung Bo,Elliott, Gregory I.
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supporting information; experimental part
p. 1546 - 1549
(2011/07/31)
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- Efficient solution-processed bulk heterojunction solar cells by antiparallel supramolecular arrangement of dipolar donor-acceptor dyes
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A series of dipolar donor-acceptor (D-A) chromophores with aminothiophene donor and different heterocyclic acceptor units is reported. By modulation of the acceptor strength, absorption bands over the whole visible spectrum are accessible as well as adjustment of the frontier molecular orbital levels. The performance of the chromophores in blends with fullerene acceptors in solution-processed bulk heterojunction solar cells was studied and related to the molecular properties of the dyes. In particular, the effect of the large ground-state dipole moments of these dyes was investigated by single crystal X-ray analysis, which revealed antiparallel dimers, resulting in an annihilation of the dipole moments. This specific feature of supramolecular organization explains the excellent performance of merocyanine dyes in organic solar cells. With blends of HB366:PC71BM, the most efficient solar cell with a VOC of 1.0 V, a JSC of 10.2 mAcm-2, and a power-conversion efficiency of 4.5% was achieved under standard AM1.5, 100 mWcm-2 conditions. Under reduced lighting conditions, even higher efficiencies up to 5.1% was obtained. Donor-acceptor dyes with an aminothiophene donor show ideal absorption, redox, and packing features in organic photovoltaics (see picture). With blends of HB366:PC71BM, highly efficient solar cells were achieved with a VOC of 1.0 V, a J SC of 10.2 mAcm-2, and a power conversion efficiency of 4.5%. Copyright
- Buerckstuemmer, Hannah,Tulyakova, Elena V.,Deppisch, Manuela,Lenze, Martin R.,Kronenberg, Nils M.,Gsaenger, Marcel,Stolte, Matthias,Meerholz, Klaus,Wuerthner, Frank
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supporting information; experimental part
p. 11628 - 11632
(2012/01/06)
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- Superacidic and HUSY-zeolite activation of 1,3-indandione: reactions with benzene and cyclohexane
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1,3-Indandione (1) readily condenses with benzene and undergoes selective ionic hydrogenation with cyclohexane when activated by superacids, such as CF3SO3H, AlCl3 and AlBr3 to give 3,3-diphenyl-1-indanone (4) and 1-indanone (7), respectively. Combination of these reactions in 'one-pot' yields 3-phenyl-1-indanone (5). In addition, similar reactions have been carried out using the regenerable solid acid, HUSY-zeolite, providing an effective excess of acidic sites. The mechanism of these reactions, with potential involvement of superelectrophilic dicationic intermediates, is discussed.
- Koltunov, Konstantin Yu.
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p. 5631 - 5634
(2008/03/11)
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- Azido-1,2,5-oxadiazoles in reactions with 1,3-dicarbonyl compounds
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The 1,3-dipolar cycloaddition of azido-1,2,5-oxadiazoles (azidofurazans) to dicarbonyl compounds was studied, and a new procedure for the synthesis of 4-R-3-(4-R1-5-R2-1,2,3-triazol-1-yl)-1,2,5-oxadiazoles was proposed.
- Batog, Lyudmila V.,Rozhkov, Vladimir Yu.,Struchkova, Marina I.
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p. 159 - 161
(2007/10/03)
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- Synthetic routes to indenothiophene, indenopyran and fluorenone derivatives
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Reaction of 3-arylaminoindene (3) with sulphur and malononitrile gave indenothiophenes (5). Hydrolysis of (5) gave (6). Condensation of (3) with malononitrile yielded (4). Treating (4d) with arylidenes (2a) afforded fluoreneimines (9). Reaction of (3) with (2a-1) yielded indenopyran (14). Hydrolysis of (14) gave (15). Also, reaction of hydrazone (16) with (2) yielded indenopyran (18), which was hydrolysed to (15). Treatment of (16) with sulphur and malononitrile or ethyl cyanoacetate afforded indenothiophen (19). Hydrolysis of (19) yielded (6). Treating indanedione dimer (22) with aromatic aldehydes and (2) afforded the arylidenes (23) and fluorenones (25) respectively.
- El-Taweel,Sofan,Ayaad,Abu El-Maati,El-Agamey
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p. 448 - 458
(2007/10/03)
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- A new synthesis of ninhydrin and its ketals using iodobenzene diacetate
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The oxidation of indene-1,3-dione (2) with iodobenzene diacetate-ROH-H2SO4, followed by the acid hydrolysis of the resulting 2,2-dialkoxyindane-1,3-diones (3), provides a new and convenient method for the synthesis of ninhydrin and its ketals.
- Prakash, Om,Sharma, Pawan K.,Saini, Neena
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p. 632 - 633
(2007/10/03)
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- Reactions with Nitrosodisulfonate, 41. Oxidation of Some Enols, Enamines, and Alcohols
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4,6-Dimethyl-1,3-cyclohexanedione is oxidized by potassium nitrosodisulfonate to the vicinal triketone 1. 5-Phenyl- and 5,5-pentamethylene-1,3-cyclohexanedione react with the aldehyde, produced by the dehydrogenation of the alcohol of the solvent, instead with the oxidant to give 2a, b and 3a. 1,2-Indanedione forms the ketol 5a, 1,3-indanedione mainly bindone.The splitting of a carbon-carbon bond is observed in the case of 2-methyl-1,3-cyclohexanedione (-> 5,6-dioxo-n-heptanoic acid), 1,2-cyclohexanedione (-> adipic acid), and dibenzyl ketone (-> benzoic acid). 1,3-Cycloheptanedione does not react.Skatole is oxidized to 2-(formylamino)-5-hydroxyacetophenone, and the Fischer base with ring enlargement to the stereoisomeric quinoline derivatives 12a and b.
- Teuber, Hans-Joachim,Hohn, Juergen,Gholami, Abbas
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p. 1309 - 1319
(2007/10/02)
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- Unusual and Competitive Side Reactions during C-Alkylation of Indan-1,3-dione
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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.
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