- Green, rapid, and highly efficient syntheses of α,α′-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]-1-indanones as potentially biologic compounds via solvent-free microwave-assisted Claisen–Schmidt condensation catalyzed by MoCl5
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A new, green, and highly efficient protocol for the expeditious preparation of some α,α′-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]-1-indanones via a simple microwave-assisted Claisen–Schmidt condensation reaction catalyzed by MoCl5 was successfully developed. Outstanding features of the current methodology include the use of solvent-free conditions, simple operation, use of a very inexpensive and available catalyst, low catalyst loading, short reaction times, high yields of the pure products, no harmful by-products, easy workup, and also the applicability of microwave irradiation as a clean source of energy. Furthermore, a gram-scale reaction was successfully conducted, proving the scalability of this current Claisen–Schmidt condensation reaction.
- Bakhshi, Reza,Zeynizadeh, Behzad,Mousavi, Hossein
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p. 623 - 637
(2019/08/26)
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- Diarylidenecyclopentanone derivatives as potent anti-inflammatory and anticancer agents
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Cancer is often associated with chronic inflammation. In order to develop potential anticancer and anti-inflammatory agents a series of 26 diarylidenecyclopentanones (DACPs) Ia–Iv, II, III, and IV were synthesized. Five of the synthesized DACPs are novel (Ih, Ij, Ik, Is, and Iv), derivative Iv was characterized using single-crystal X-ray diffraction study. All the synthesized derivatives were tested for their anti-inflammatory as well as cytotoxicity properties. Compound Is is found to have the highest anti-inflammatory activity (93.67%) by inhibiting PGE2 (prostaglandin E2) production. Three of the DACPs (Io, It, and Iu) were observed to have high cytotoxicity with IC50 value of 8.73 ± 0.06 μM (Io), 12.55 ± 0.31 μM (It), and 11.47 ± 0.15 μM (Iu) against HeLa cells. Further staining and cell cycle analysis was done using these three DACPs to understand their mechanism of action. The G0/G1 phase was observed to be the longest one through which the cells undergo apoptosis.
- Tamang, Nitesh,Ramamoorthy, Gayathri,Joshi, Mayank,Choudury, Angshuman Roy,B, Siva Kumar,Golakoti, Nageswara Rao,Doble, Mukesh
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p. 1579 - 1589
(2020/07/02)
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- Second- and third-order nonlinear optical properties of Bis-chalcone derivatives
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Bis-chalcone derivatives: 2,5-bis(benzylidene)-cyclopentanone (CP-DBA), 2,5-bis(4-methoxy-benzylidene)-cyclopentanone (CP-POME), 2,5-bis(4-isopropyl- benzylidene)-cyclopentanone (CP-ISO) and 2,5-bis(cinnamylidene)-cyclopentanone (CP-CAL) are synthesized by Claisen-Schmidt reaction and characterized using, FT-IR, 1H NMR, 13C NMR, and mass spectroscopic techniques. The second- and third-order nonlinear optical properties of these samples are studied using second harmonic generation and nanosecond open-aperture Z-scan methods. CP-POME has shown a very high second harmonic generation (SHG) efficiency (5.3 times that of urea). These molecules reveal a strong third-order nonlinear absorption (NLA) that is of optical limiting type, due to their peculiar D-π-A-π-D structure that leads to high polarization of the delocalized electron cloud. CP-CAL exhibits highest NLA activity with a β coefficient of 1 × 10-10 m/W. Through numerical simulations, the mechanism of NLA is found to be a two-photon absorption process in the case of all the samples.
- Sai Kiran,Anand, Benoy,Siva Sankara Sai,Nageswara Rao
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- Aldol condensations of a variety of different aldehydes and ketones under ultrasonic irradiation using poly(N-vinylimidazole) as a new heterogeneous base catalyst under solvent-free conditions in a liquid-solid system
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An ultrasound-assisted aldol condensation reaction has been developed for a range of ketones with a variety of aromatic aldehydes using poly(N-vinylimidazole) as a solid base catalyst in a liquid-solid system. The catalyst can be recovered by simple filtration and reused at least 10 times without any significant reduction in its activity. The reaction is also amenable to the large scale, making the procedure potentially useful for industrial applications.
- Khaligh, Nader Ghaffari,Mihankhah, Taraneh
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p. 2167 - 2173
(2014/01/06)
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- Sulfuric acid-modified PEG-6000 (PEG-SO3H): An efficient, bio-degradable and reusable catalyst for synthesis of α, α′ bis(arylidene) cycloalkanones under solvent-free conditions
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A green and efficient method for synthesis of α, α′ -bis (arylidene) cycloalkanones, starting from aromatic aldehydes in reaction with ketones using sulfonated polyethylene glycol 6000 (PEG-SO3H) as a stable, reusable and biodegradable catalyst under solvent-free conditions at 80 °C is described. The use of a nontoxic, inexpensive, easily available and recyclable catalyst makes this protocol practical, environmentally friendly and economically attractive.
- Nasseri, Mohammad A.,Salimi, Mehri
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p. 164 - 170
(2013/07/26)
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- A convenient synthesis of α,α'-bis(substituted benzylidene)cycloalkanones Catalyzed by Y(TFA) 3
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Aromatic aldehydes undergo crossed aldol condensation with cyclic ketones in the presence of Y(TFA)3 under solvent-free conditions to afford the corresponding α,α-bis(substituted benzylidene)cycloalkanones in satisfactory yields. Furthermore, the catalyst can be recovered conveniently and reused several times in the reaction with comparable yields. Copyright Taylor & Francis Group, LLC.
- Luo, Genxiang,Wang, Runxia,Liu, Chunsheng
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experimental part
p. 554 - 556
(2012/06/30)
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- Solvent-free, cross-aldol condensation reaction using silica-supported, phosphorus-containing reagents leading to α,α′-Bis(arylidene) cycloalkanones
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This article describes an efficient, simple, and clean method for the synthesis of α,α′-bis(arylidene, furylidene and cinnamylidene)cycloalkanones under solvent-free conditions. The cross-aldol condensation of cycloalkanones with aldehydes in the presence of silica-supported phosphorus pentoxide (P2O5/SiO 2) or silicaphosphinoxide (silphox, [POCl3-n(SiO 2)n]) as heterogeneous reagents produces the title compounds in good to excellent yields. Copyright Taylor & Francis Group, LLC.
- Hasaninejad, Alireza,Zare, Abdolkarim,Balooty, Laleh,Mehregan, Hadis,Shekouhy, Mohsen
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experimental part
p. 3488 - 3495
(2011/02/22)
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- An efficient and practical procedure for synthesis of α, α′-bis(substituted benzylidene)cycloalkanones catalyzed by solid base SiO2-OK
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The condensation of cycloalkanones with aromatic aldehydes catalyzed by solid base SiO2-OK in refluxing EtOH, result in the formation of the corresponding α,α′-bis(substituted benzylidene)cycloalkanones in good to excellent yields.
- Jin, Tong-Shou,Zhao, Ying,Liu, Li-Bin,Li, Tong-Shuang
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p. 1965 - 1967
(2007/10/03)
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- Synthesis of α, α′-bis(substituted benzylidene)ketones catalysed by a SOCl2/EtOH reagent
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The cross-aldol condensations of cyclopentanone, cyclohexanone and acetone with benzaldehyde or cinnamaldehyde were catalysed in the presence of SOCl 2, in anhydrous ethanol to synthesise α, α′ -bis(substituted benzylidene) ketones with excellent yields(92-97%).
- Hu, Zhi Guo,Liu, Jun,Zeng, Ping Li,Dong, Zhi Bing
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- SmI3 catalyzed condensation of aliphatic cycloketones and aldehydes in ionic liquid
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SmI3 catalyzed condensation of aliphatic cycloketones and aldehydes was studied in ionic liquid. 2,5-Dibenzyldiene cyclopentanones and 2,6-dibenzyldienecyclohexanones were prepared in high yields under convenient conditions.
- Zheng, Xingliang,Zhang, Yongmin
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p. 161 - 165
(2007/10/03)
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- A facile synthesis of α,α'-bis(substituted benzylidene)cycloalkanones catalyzed by bis(p-ethoxyphenyl)telluroxide(BMPTO) under microwave irradiation
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The bis(4-methoxyphenyl)telluroxide(BMPTO) catalyzed reaction of cyclopentanone or cyclohexanone with aldehydes brought about the cross-aldol condensation to give the corresponding 2,5-bis(substituted benzylidene)cyclopentanones or 2,6-bis(substituted benzylidene)cyclohexanones in high yield under microwave irradiation in mild conditions. The reaction needs only 5-10 min.
- Zheng, Ming,Wang, Longcheng,Shao, Jianguo,Zhong, Qi
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p. 351 - 354
(2007/10/03)
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- A facile route to synthesize α,α'-bis(substituted-benzylidene) cycloalkanones promoted by SmI3
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Promoted by SmI3 cycloalkanone trimethylsilyl enol ethers were reacted with aldehydes to give α,α-bis(substituted-benzylidene) cycloalkanones.
- Bao, Weiliang,Zhang, Yongmin,Ying, Taokai
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p. 503 - 507
(2007/10/03)
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- Synthesis and Properties of Substituted Dicinnamylidene Cycloketones
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Different substituted dicinnamylidene cycloketones were synthesized via base-catalyzed condensations of substituted cinnamaldehydes and different cycloketones.The reaction products were identified on the basis of their infrared, proton and carbon-13 nucle
- Al-Arab, Mohammad M.,Abu-Yousef, Imad A.
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p. 137 - 139
(2007/10/02)
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