19744-83-3Relevant articles and documents
Bronsted acidic ionic liquids promoted cyclocondensation reaction: Synthesis of 1,8-dioxo-octahydroxanthene
Salvi,Mandhare,Sartape,Pawar,Han,Kolekar
, p. 883 - 886 (2011)
Novel Bronsted acidic ionic liquids bearing hydrogen sulfate and dihydrogen phosphate as anions were designed and successfully applied as catalysts for the one-pot synthesis of 1,8-dioxo-octahydroxanthene in water medium. The sequence of the catalytic act
Microwave assisted synthesis and crystal structure of 3,3,6,6-tetramethyl- 9-(phenyl)-1,8-dioxo-2,3,4,5,6,7-hexahydroxanthene
Rao, Xiao-Ping,Wu, Yong,Song, Zhan-Qian,Shang, Shi-Bin
, p. 500 - 503 (2009)
The title compound (C23H26O3, M r = 350.44) has been synthesized under microwave irradiation. Its structure was characterized by IR, 1H NMR spectroscopy and single-crystal X-ray diffraction. The title
Diversity Oriented Synthesis of Polycyclic Heterocycles through the Condensation of 2-Amino[1,2,4]triazolo[1,5-a]pyrimidines with 1,3-Diketones
Pyatakov, Dmitry A.,Sokolov, Andrey N.,Astakhov, Alexander V.,Chernenko, Andrey Yu.,Fakhrutdinov, Artem N.,Rybakov, Victor B.,Chernyshev, Vladimir V.,Chernyshev, Victor M.
, p. 10694 - 10709 (2015)
The acid-catalyzed condensation between 2-aminosubstituted [1,2,4]triazolo[1,5-a]pyrimidines and their analogues with various saturation of the pyrimidine ring and 1,3-diketones or 1,1,3,3-tetramethoxypropane was evaluated as a new approach for the synthesis of diversely substituted polycyclic derivatives of triazolopyrimidine. The reaction of 4,5,6,7-tetrahydro- or aromatic aminotriazolopyrimidines results in selective formation of the corresponding [1,2,4]triazolo[1,5-a:4,3-a′]dipyrimidin-5-ium salts, and the condensation of substrates containing the 4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine fragment is accompanied by a cascade rearrangement with unusual recyclization of the dihydropyrimidine ring to yield partially hydrogenated [1,2,4]triazolo[1,5-a:4,3-a′]dipyrimidin-5-ium or pyrimido[1′,2′:1,5][1,2,4]triazolo[3,4-b]quinazolin-5-ium salts. The proposed methodology exhibits a wide scope, providing rapid access to polycondensed derivatives of the [1,2,4]triazolo[1,5-a]pyrimidine scaffold. DFT calculations of the Gibbs free energies of possible isomers were performed to rationalize the experimentally observed reactivity and selectivity.
Efficient and clean synthesis of 1,8-dioxooctahydroxanthenes in aqueous medium
Pore, Santosh B
, p. 2621 - 2624 (2018)
In this work, an efficient synthesis of 1,8-dioxooctahydroxanthenes in aqueous medium is reported. The reaction was catalyzed by aqueous extract of plant material (pericarp of Sapindus trifoliatus fruit), which makes this protocol 'green' and eco-friendly
Efficient synthesis of decahydroacridine-1,8-diones and polyhydroquinolines using the step-wise method
Hosseininasab, Fatemeh Sadat,Memarian, Hamid Reza
, p. 1515 - 1540 (2022/01/11)
Various symmetrical and unsymmetrical decahydroacridine-1,8-dione and polyhydroquinoline derivatives were synthesized via two-step cyclocondensation reactions. The advantages of this step-wise addition of reactants in comparison with other one-pot reactions are avoiding the formation of 2 or 3 undesired by-products, therefore allowing cleaner work up of reaction. The important factor of this effective cyclocondensation method is that the prepared β-enaminone component was added dropwise to the solution, in which the Knoevenagel condensation product is slowly being formed by reaction of aldehyde molecule and 1,3-dicarbonyl compounds. The results of the proposed step-wise method are compared and discussed with those obtained in the one-pot reactions.
Sustainable synthesis of 1,8-dioxooctahydroxanthenes in deep eutectic solvents (DESs)
Shaibuna,Abbas, Anshad,Kariyottu Kuniyil, Muhammed Jeneesh,Sreekumar
, p. 8335 - 8344 (2021/05/21)
Deep eutectic solvents are obtained by the fusion of two or more compounds: hydrogen bond donors (HBDs) and hydrogen bond acceptors (HBAs). They are formed by mixing the constituents with moderate heating (via hydrogen bond interactions). In this manuscript, the dual activities (as catalysts and reaction media) of six deep eutectic solvents were compared for the synthesis of 1,8-dioxooctahydroxanthenes at room temperature. Here DES 2, a combination of ZrOCl2·8H2O with ethylene glycol at a 1 : 2 ratio, was found to be the supreme catalyst among the six DESs and was reused for five batches. The photophysical properties of the xanthene derivatives were examined by UV-vis and fluorescence spectroscopy in THF. The synthesised molecules showed absorption maxima around 285-295 nm and emission maxima around 403-404 nm. The ground state dipole moments of all the molecules were calculated by the Debye-Guggenheim method using toluene as the non-polar solvent. All the synthesised molecules showed significant dipole moment values and are in good agreement with theoretical values.
