938-24-9Relevant articles and documents
Synthesis, characterization, and some reactions of the tricarbonylchromium complexes of 1,3-indandione and ninhydrin
Leinweber, Dirk,Wartchow, Rudolf,Butenschoen, Holger
, p. 167 - 179 (1999)
The syntheses and characterization of the tricarbonylchromium complexes of 1,3-indandione and ninhydrin are described. As the direct complexation proved unsuccessful, the acetal route was tried. Although some complexes were obtained, complex deacetalization did not work in the case of ninhydrin. Finally, the oxidation of tricarbonyl(η6-1,3-indandione)chromium(0) with dimethyldioxirane gave the ninhydrin complex in 75% yield in equilibrium with the indantrione complex. The latter reacts in hetero Diels-Alder reactions with dienes with diastereoselective formation of spiro anellated pyran derivatives.
One-step stereoselective synthesis of dialkyl 1,1-diacetyl-8a-hydroxy-8- oxo-1,2,8,8a-tetrahydrocyclopenta[a]indene-2,3-dicarboxylates from the reaction of dialkyl 2-(1-acetyl-2-oxopropyl)-3-(tributylphosphoranylidene) succinates with indene-1,2,3-trione
Ramazani, Ali,Ahmadi, Ebrahim,Noshiranzadeh, Nader
, p. 2285 - 2290 (2005)
Protonation of the highly reactive 1:1 intermediates produced in the reaction between tributylphosphine and dialkyl acetylenedicarboxylates by acetylacetone leads to sterically congested phosphorus ylides that undergo an intermolecular addition reaction with indene-1,2,3-trione and concomitant intramolecular Wittig reaction in CH2Cl2 at room temperature to produce dialkyl 1,1-diacetyl-8a-hydroxy-8-oxo-1,2,8,8a- tetrahydrocyclopenta[a]indene-2,3-dicarboxylates in fairly good yields. Copyright Taylor & Francis Inc.
Total 2p? Spin Density Mapping as a Function of Hydrogen Bonding Involving an Anion Radical
Reiter, Richard C.,Stevenson, Gerald R.,Wang, Zhong Yi
, p. 5717 - 5720 (1990)
EPR spectra will utilized to generate a "map" of the 2p? spin density distribution in the indanetrione anion radical as a function of hydrogen bond formation between this anion radical and water. 17O substitution followed by computer simulation of natural abundance 13C splittings and enriched 17O splittings allowed measurements of the spin densities on each atom of the radical.The four observable 13C hyperfine splittings were found to vary upon hydrogen bond formation, and the equilibrium constant for hydrogen bonding (C9H4O3.- + HOH = C9H4O3.-...HOH) could be evaluated from the variation in these splittings.However, the 2p? spin densities on only three of the seven nonequivalent positions are perturbed.The 2p? spin densities on the two oxygen atoms are invariant even though the formation of the hydrogen bond involves the oxygen atoms.
Design, synthesis, and characterization of oxadiazolopyrazine analogs with application as anticancer agents
Chang, Tzu-Ting,Chen, Chia-Ling,Chen, Wei-Chia,Chen, Wei-Sheng,Hsieh, Feng-Chun,Li, Wen-Shan
, (2021/12/23)
Here, we describe the synthesis and evaluation of a class of cell-permeable indeno-oxadiazolopyrazine analogs as the anticancer agents. A new and facile approach to the synthesis of substituted analogs of indeno-oxadiazolopyrazine is illustrated. We find that the designed indeno-oxadiazolopyrazines, 3, 4, 10, 11, 15, and 16, act as potent anticancer agents compared to camptothecin, topoisomerase I inhibitor. These observations suggest that the electron-donating group (methoxy) at the C-5, C-6, and C-8 positions or electron-withdrawing group (fluoro) at the C-6 and C-7 positions on the A ring of indeno-oxadiazolopyrazines is required for antiproliferative activities against MDA-MB-231, BT549, and MCF7 cell lines.
Diastereoselective synthesis of novel spiro indanone fused pyrano[3,2-: c] chromene derivatives following hetero-Diels-Alder reaction and in vitro anticancer studies
Panda, Pravati,Nayak, Sabita,Sahoo, Susanta Ku.,Mohapatra, Seetaram,Nayak, Deepika,Pradhan, Rajalaxmi,Kundu, Chanakya Nath
, p. 16802 - 16814 (2018/05/23)
The development of concise methods for the synthesis of small functionalised spirocyclic molecules is important in the search of new bioactive molecules. To contribute this, here we represent a diastereoselective oxa-hetero-Diels-Alder reaction for the synthesis of novel spiro indanone fused pyrano[3,2-c]chromene derivatives and studied their in vitro anticancer activities. Using previously less explored cyclic ketone i.e. indane-1,3-dione and 3-vinyl-2H-chromene derivatives, we obtained novel spiro-heterocyclic frameworks at the interphase between "drug-like" molecules and natural products. Various spiro indanone fused pyrano[3,2-c]chromene derivatives were synthesized regiospecifically bearing a quaternary stereocenter in high yields (up to 85%) with excellent diastereoselectivity in toluene using 4 ? MS as additive under reflux condition at 120 °C. In vitro cytotoxic studies of these compounds against MCF-7 (breast cancer), HCT-116 (colon cancer), H-357 (oral cancer), MD-MB-231(Breast cancer) cell lines were evaluated by MTT {3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide} assay in vitro. The screening results revealed that many of the compounds are showing moderate to high levels of anticancer activities against the tested cancer cell lines and some displayed potent inhibitory activities in comparison to the commercial anticancer drug 5-fluorouracil (5-FU). Among the series, compound 3′c showed most potent cytotoxicity (15.0-27.5 μM) in three cancer cell lines (MCF-7, HCT-116 and MD-MB-231).
Facile synthesis of 1,2,3-tricarbonyls from 1,3-dicarbonyls mediated by cerium(IV) ammonium nitrate
Sivan, Akhil,Deepthi, Ani
supporting information, p. 1890 - 1893 (2014/03/21)
A mild and efficient protocol for the synthesis of vicinal tricarbonyl compounds from β-dicarbonyls in a single step using cerium(IV) ammonium nitrate as a catalytic oxidant is described. Ease of execution, wide substrate scope and the suitability for the synthesis of commercially important compounds like ninhydrin, alloxan and oxoline make this reaction particularly noteworthy.
Photolysis of indan-l,2-dione derivatives in oxygen-doped argon matrix at low temperature
Itoh, Takayoshi,Tatsugi, Jiro,Tomioka, Hideo
experimental part, p. 475 - 481 (2009/08/07)
Photolysis of indan-l,2,3-trion (la), benzo[ft]furan-2,3-dione (lb), and N-methylisatin (1c) in argon matrix either with or without oxygen at 10 K was investigated by IR spectroscopy in combination with DFT calculations. The results indicate that while 1a and 1b gave the products mixture as a result of α-cleavage, followed by decarbonylation, 1c was rather photostable under similar conditions. However, when the irradiation was carried out in argon matrix doped with 20% oxygen, 1c decomposed much more efficiently than that in argon matrix and cyclic diacyl peroxide presumably formed by trapping of initial diradical originating from α-cleavage by molecular oxygen was detected. Similar irradiation of 1b also gave cyclic diacyl peroxide along with photodecarbonylation products, but irradiation of 1a in oxygen-doped matrix produced not only cyclic diacyl peroxide but also products as a result of oxidation of photodecarbonylation product. The present observation reveals that photolysis of ketones in oxygen-doped matrix at low temperature provides useful information concerning the reactivities of ketones toward α-cleavage.
Ozonolysis of enol ethers. Part 10. Ozonization of enol ethers from 1,2- and 1,3-dicarbonyl compounds: Direct quantitative synthesis of phthalonic acid anhydride
Schank, Kurt,Beck, Horst,Pistorius, Susanne
, p. 2025 - 2049 (2007/10/03)
The results of ozonolyses of enol ethers from 1.2- and 1.3-dicarbonyl compounds presented here strongly indicate that these reactions do not proceed via the established Criegee ozonolysis mechanism for nucleophilic C=C bonds. The quantitative one-step synthesis of phthalonic acid anhydride via ozonolysis of 2-(methoxymethyliden)-1H-inden-1.3(2H)-dione (28a) is described. Furthermore, a revision of the theory of alkene ozonolysis in the presence of tetracyanoethylene (TCNE) is proposed on the basis of a single-electron-transfer (SET) chemistry.
A convenient one-pot synthesis of Indane-1,2,3-triones by oxidation of indan-1-ones with N-bromosuccinimide-dimethyl sulfoxide reagent
Tatsugi, Jiro,Izawa, Yasuji
, p. 859 - 864 (2007/10/03)
Indane 1,2,3-triones (2(a-f)) have been synthesized via brommation of indan-1-ones (1(a-f)), followed by oxidation of the resulting brominated indan-1-ones with dimethyl sulfoxide in one pot in good yields.
Photochemical behavior of indane-1,2,3-trione in degassed alcoholic solutions: Formation of 3-substituted phthalides
Tatsugi, Jiro,Hara, Tomoaki,Izawa, Yasuji
, p. 177 - 178 (2007/10/03)
Irradiation of indane-1,2,3-trione in degassed alcoholic solutions affords 3-alkoxycarbonylphthalides as the major product together with 3-alkoxyphthalides. 3-Alkoxycarbonylphthalides may be derived from the reaction between alcohols and the spirooxiranone intermediate, generated photochemically by cleavage of the bond between two carbonyl groups of indane-1,2,3-trione via a cyclobutenone biradical derivative.
