10321-25-2Relevant articles and documents
A facile synthesis of α,α′-bis(substituted benzylidene) cycloalkanones catalyzed by KF/Al2O3 under ultrasound irradiation
Li, Ji-Tai,Yang, Wen-Zhi,Chen, Guo-Feng,Li, Tong-Shuang
, p. 2619 - 2625 (2003)
The condensation of the cyclopentanone or cyclohexanone with aromatic aldehydes catalyzed by KF/Al2O3 in MeOH under ultrasound irradiation, result the corresponding 2,5-bis(substituted benzylidene) cyclopentanones or 2,6-bis(substituted benzylidene) cyclohexanones in good yields.
Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α′-bis(arylidene)cycloalkanones
Ahmadi, Salimeh,Zare, Abdolkarim,Aali-Hosaini, Mina,Maghsoudi, Maryam,Izadpanah, Shadi,Parhami, Abolfath,Merajoddin, Maria
, p. 6245 - 6253 (2016)
Abstract: The aim of this work is to introduce a novel and attractive protic acidic ionic liquid as catalyst for organic synthesis. To achieve this aim, N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} was prepared by reaction of NEt3 with ClSO3H and then with H2SO4. The novel acidic ionic liquid was identified by Fourier-transform infrared (FT-IR), 1H nuclear magnetic resonance (NMR), 13C NMR, and mass spectroscopies. Its catalytic activity was then examined in the cross-aldol condensation reaction of arylaldehydes with cycloalkanones under solvent-free conditions, obtaining α,α′-bis(arylidene)cycloalkanones in high yield after short reaction time. Graphical Abstract: [Figure not available: see fulltext.]
Animal bone meal as an efficient catalyst for crossed-aldol condensation
Riadi,Mamouni,Azzalou,Boulahjar,Abrouki,El Haddad,Routier,Guillaumet,Lazar
, p. 6715 - 6717 (2010)
α,α′-Bis(substituted benzylidene)cycloalkanones were efficiently prepared from cycloalkanones and benzaldehydes in water by using animal bone meal (ABM) or ABM modified as a catalyst. It is shown that ABM modified can be quantitatively recovered and be reused effectively for many times. A comparison of catalytic activity of these catalysts is discussed.
KF-melamine formaldehyde resin (KF-MFR) as a versatile and efficient heterogeneous reagent for aldol condensation of aldehydes and ketones under microwave irradiation
Rezaie, Ramin,Heidary, Mohammad,Soltani Rad, Mohammad Navid,Behrouz, Somayeh
, p. 1221 - 1226 (2011)
KF-Melamine formaldehyde resin (KF-MFR) was demonstrated to be a highly efficient heterogenious catalyst for cross-aldol condensation under microwave irradiation. In this synthesis, various aldehydes and ketones were condensed together in the presence of supported KF on melamine-formaldehyde resin to afford different chalcone derivatives in good to excellent yields. KF-MFR proved to have unique termal and chemical resistance and can be reused for many consecutive runs without remarkable loss in catalytic activity. Copyright
Solvent-free crossed aldol condensation of cyclic ketones with aromatic aldehydes assisted by microwave irradiation
Esmaeili, Abbas A.,Tabas, Mehri Salimi,Nasseri, Mohammad A.,Kazemi, Foad
, p. 571 - 576 (2005)
A fast alumina-promoted crossed aldol-condensation reaction of aldehydes and cyclic ketones under microwave irradiation is described. This process is simple, efficient, and environmentally benign and proceeds in fairly high yield without any self-condensation. Springer-Verlag 2005.
α,α′-bis(benzylidene)cycloalkanones by condensation in water under PTC catalysis and microwave irradiation
Zhou, Jianfeng
, p. 75 - 79 (2005)
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Synthesis of air-stable mixed bis-carboxylate titanocene complexes and their catalytic behaviors in cross-aldol and Mannich reactions
Wang, Jing,Chen, Xi,Wang, Xiu,Zhang, Wei-Qiang,Sun, Hua-Ming,Zhang, Guo-Fang,Wu, Ya,Gao, Zi-Wei
, p. 731 - 738 (2016)
Tunable organometallic Lewis acid catalysts were developed by combining salicylic acid (H2-Sal) with benzoic acid (H-Ben), 4-fluorobenzoic acid (H-BenF) and 3-thiophenic acid (H-Th), as coligands for mixed bis-carboxylate titanocene complexes. Three air-stable complexes [Cp2Ti(η1-HSal)(η1-Ben)] (1), [Cp2Ti(η1-HSal)(η1-BenF)] (2) and [Cp2Ti[η1-HSal][(η1-Th)] (3) were prepared in high yields by the reaction of salicylato titanocene chelate with carboxylate ligands. The mixed bis-carboxylate titanocene complexes were fully characterized by physicochemical and spectroscopic methods. Single-crystal X-ray diffraction studies revealed Ti–O(H-Sal) bond distances in 1, 2 and 3 of 1.972(3), 1.9245(18) and 1.912(5)??, respectively, while the bond distances involving the coligands of 1, 2 and 3 are 1.908(3)?? (Ti–OBen), 1.9296(19)?? (Ti–OBenF) and 1.945(5)?? (Ti–OTh), respectively. These bis-carboxylate titanocene complexes showed satisfactory activities and selectivities in Mannich and cross-aldol reactions. Notably, complex 3 bearing the labile thiophene carboxylate ligand gave high yields with a diastereomer ratio (d.r.) as high as 1:99 for the direct Mannich reactions of benzaldehyde, cyclohexanone and aniline. In cross-aldol reaction of benzaldehyde and cyclohexanone, 1 and 2 successfully catalyzed the formation of double-aldol products in up to 99?% yield.
Indium trichloride catalyzes aldol-condensations of aldehydes and ketones
Deng, Guisheng,Ren, Tiegan
, p. 2995 - 3001 (2003)
InCl3·4H2O catalyzes the cross-aldol condensation of different ketones with various aldehydes to give α,β-unsaturated carbonyl compounds in good to excellent yields.
Synthesis of thiazolylidenethiazoloquinazolinone hybrids from monocarbonyl curcumin analogues. Characterization, bio-evaluation and DFT study
Benreka, Soufiane,Zradni, Fatima-Zohra,Madi, Fatiha,Kirsch, Gilbert,Kasmi-Mir, Souad
, p. 53 - 77 (2021/09/03)
Given the diverse pharmacological attributes possessed by the curcumin and its analogs, quinazolinethione 3, thiazoloquinazolinone 4, and thiazolylidene thiazoloquinazolinone hybrids D1-D12 were synthesized from α, α’ Bis(arylidene)Cyclohexanone (BAC) as starting material. The proposed structures of all synthesized compounds were confirmed by 1H, 13CNMR, and elemental analysis. The newly synthesized hybrids were screened in vitro for their antimicrobial and antioxidant activities. Preliminary studies showed that compounds D4, D5, D10, D11, and D12 exhibited superior inhibitory behaviors against some microorganisms in comparison with standard drugs. In addition, DPPH radical scavenging assay was used to evaluate their antioxidant property. Accordingly, compound D11 was found to be a more powerful antioxidant than the other compounds. Furthermore, the HOMO–LUMO energy values and some chemical parameters indicate that the synthesized hybrid D11 is more reactive than D7. These results were consistent with our experimental data on antioxidants. Moreover, molecular electrostatic potential (MEP) maps were computed in order to predict the reactive sites for nucleophilic and electrophilic attacks of the synthesized hybrids D7 and D11.
Ash of pomegranate peels (APP): A bio-waste heterogeneous catalyst for sustainable synthesis of α,α′-bis(substituted benzylidine)cycloalkanones and 2-arylidene-1-tetralones
Patil, Rupesh C.,Patil, Uttam P.,Jagdale, Ashutosh A.,Shinde, Sachinkumar K.,Patil, Suresh S.
, p. 3527 - 3543 (2020/05/13)
Abstract: α,α′-bis(substituted benzylidene)cycloalkanones were efficiently prepared from variously substituted aldehydes and cycloalkanones in water by using ash of pomegranate peels (APP) as a catalyst. The APP-catalyst was obtained from bio-waste by simple thermal treatment to dry peels of pomegranate fruit and formation of its active phase was confirmed by FT-IR, XRD, XRF, EDX, SEM, DSC-TGA and BET techniques. The analysis revealed that the present catalyst has basic sites which promote the synthesis of desired products. The main attractions of our protocol are utilization of highly abundant bio-waste-derived catalyst and good-to-excellent yield in shortest reaction time. This green protocol was further extended for structurally diverse 2-arylidene-1-tetralones by condensation of equimolar quantity of aromatic aldehydes and 1-tetralone at low temperature. The catalyst could be quantitatively recovered and reused effectively for five times. Graphic abstract: [Figure not available: see fulltext.].
