- 1,8-Diazabicyclo [5.4.0] undec-7-ene functionalized cellulose nanofibers as an efficient and reusable nanocatalyst for the synthesis of tetraketones in aqueous medium
-
Abstract: 1,8-Diazabicyclo [5.4.0] undec-7-ene functionalized cellulose nanofibers (CNF@DBU[Cl]) were simply prepared and characterized by analytical techniques. Scanning electron microscope confirmed that CNF@DBU[Cl] was formed with average size of 30–60?nm. X-ray diffraction of CNF@DBU[Cl] showed that the crystalline structure of the cellulose nanofibers was remained unchanged after functionalization. According to elemental analyses and thermal gravimetric analysis, the loading amount of organic group on cellulose nanofibers was found to be 1.46?mmol/g. The catalytic activity of DBU functionalized cellulose nanofibers was studied for the synthesis of biologically important tetraketone derivatives in the reaction of aldehydes with 1,3-dicarbonyl compounds. In the presence of CNF@DBU[Cl], the corresponding tetraketones were obtained in 80–96% yields under very mild reaction conditions. The catalyst was recovered and reused four successive runs without significant loss of catalytic activity. This method showed several significant advantages including short reaction times, high yields of products, use of various substrates, convenient work-up, no necessity of extraction or chromatographic purification steps, environmentally friendly conditions and lack of use of any harmful solvent. Graphic abstract: [Figure not available: see fulltext.].
- Lasemi, Zahra,Tajbakhsh, Mahmood,Alinezhad, Heshmatoallah,Mehrparvar, Forough
-
p. 3667 - 3682
(2020/05/13)
-
- Enhanced catalytic activity of bio-fabricated ZnO NPs prepared by ultrasound-assisted route for the synthesis of tetraketone and benzylidenemalonitrile in hydrotropic aqueous medium
-
Abstract: Mushroom-like mesoporous and hexagonal ZnO nanoparticles were synthesized from plant extract and chemical method respectively, by co-precipitation method in aqueous medium. Different morphological forms of ZnO NPs were characterized by XRD, TGA, FESEM, EDX, FTIR, UV–Vis and BET. Neem (Azadirachta indica) leaf extract and ultrasound irradiation have a crucial role in the formation of different morphologies of ZnO NPs. ZnO NPs synthesized from plant extract and hydrotrope show a synergistic effect that leads to efficient synthesis of benzylidenemalonitrile and tetraketone derivatives at room temperature in water. Simple preparation of the catalyst, excellent yields, reusability of catalyst with consistent activity and ease of product isolation are the most significant advantages of this green protocol. Graphic abstract: [Figure not available: see fulltext.]
- Attar, Suraj R.,Kamble, Santosh B.,Shinde, Bipin
-
-
- Zinc-containing ionic liquid as a dual solvent-catalyst in base-free condensations under ultrasonic irradiation
-
In this study, natural-based ionic liquid (IL) using caffeine (Caff), trietahnolamine (TEA) and ZnBr2, [Caff-TEA]+[ZnBr3]?, which features high catalytic activity and environmentally-friendly nature was synthesized with melting point of 76?°C by a facile method. The synthesized [Caff-TEA]+[ZnBr3]? has high catalytic activity as both of catalyst and solvent in condensation reactions for the synthesis of benzylidenes, bis-hydroxyenones and xanthenes. Synthesized IL was characterized by proton nuclear magnetic resonance (1HNMR), Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD) and Energy-dispersive X-ray spectroscopy (EDX) analysis. Also synthesized heterocycles were characterized by FT-IR, proton nuclear magnetic resonance (1HNMR) and carbon nuclear magnetic resonance (13CNMR).
- Ghafuri, Hossein,Yaghoubi, Soheila,Zand, Hamid Reza Esmaili
-
-
- Nickel NPs @N-doped titania: an efficient and recyclable heterogeneous nanocatalytic system for one-pot synthesis of pyrano[2,3-d]pyrimidines and 1,8-dioxo-octahydroxanthenes
-
Abstract: Catalysis holds a very important and promising place in chemical industry. In a typical chemical transformation, the use of a catalyst reduces the reagent-based waste and enhances the reaction selectivity, thereby minimizing the chances of getti
- Rajinder, Yogayta,Gupta, Monika,Kour, Jaspreet
-
p. 1977 - 1992
(2019/04/30)
-
- Anion functionalized ionic liquid from artificial sugar: A sustainable pathway for diverse bis-enol derivatives
-
An artificial sugar saccharine based anion-functionalized ionic liquid [Bmim]Sac was synthesized and used for new and straightforward strategies for the construction of a diverse range of bis-enols. The advantage of this methodology is the use of a non-to
- Sharma, Himani,Srivastava, Suman
-
supporting information
p. 12054 - 12058
(2019/08/07)
-
- An efficient synthesis of 2,2'-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) derivatives using Baker's yeast**
-
A simple and efficient method was developed for the synthesis of 2,2'-arylmethylene dicyclohexane-1,3-dione derivatives via the Knoevenagel–Michael cascade reactions of aromatic aldehydes and 5,5-dimethyl-1,3-cyclohexanedione catalyzed by Saccharomyces ce
- Ashtarian, Jahanbakhsh,Heydari, Reza,Maghsoodlou, Malek-Taher,Yazdani-Elah-Abadi, Afshin
-
p. 259 - 263
(2019/07/31)
-
- Selective and highly efficient synthesis of xanthenedione or tetraketone derivatives catalyzed by ZnO nanorod-decorated graphene oxide
-
ZnO nanorod-decorated graphene oxide (GO/ZnO), containing Lewis and Bronsted acid centers, was introduced as a selective, highly efficient and recoverable nanocatalyst for the pseudo three-component synthesis of diverse tetraketone or xanthenedione derivatives via condensation of aromatic aldehydes with 1,3-dicarbonyl compounds in short reaction times and good to excellent yields in H2O under refluxing and solvent-free conditions, respectively. Moreover, the GO/ZnO nanocomposite was recovered and reused at least four times without a significant decrease in its activity. Low loading of the catalyst, high to excellent yields, the elimination of any toxic heavy metals or corrosive reagents for modification of the catalyst, simple separation and purification of the products, and the reusability of the catalyst are the most significant advantages of this green protocol. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018.
- Hasanzadeh Banakar, Sepideh,Dekamin, Mohammad G.,Yaghoubi, Amene
-
p. 14246 - 14262
(2018/08/29)
-
- Synthesis of Tetraketones Using ZnS Nanoparticles as an Efficient Catalyst
-
An efficient pseudo-three-component synthesis of tetraketones is described by one-pot condensation of 5,5-dimethylcyclohexane-1,3-dione and aldehydes using ZnS nanoparticles at room temperature. This method provides several advantages such as mild reactio
- Safaei-Ghomi, Javad,Asadian, Saeedeh,Nazemzadeh, Seyed Hadi,Shahbazi-Alavi, Hossein
-
p. 430 - 434
(2017/12/28)
-
- Transition metal and base free coupling of N-tosylhydrazones with 1,3-dicarbonyl compound
-
N-tosylhydrazones derived from a wide variety of aryl, alkyl and heteroaryl aldehydes undergo smooth coupling with 5,5-dimethylcyclohexane-1,3-dione under transition metal and base free conditions to generate tetraketo compounds in high yields. In presenc
- Choudhary, Deepika,Agrawal, Chanchal,Khatri, Vineeta,Thakuria, Ranjit,Basak, Ashok K.
-
supporting information
p. 1132 - 1136
(2017/03/02)
-
- In water–ultrasound-promoted synthesis of tetraketones and 2-substituted-1H-benzimidazoles catalyzed by BiOCl nanoparticles
-
A highly efficient, green protocol has been developed for the synthesis of various structurally diverse 2,2′-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) and 2-substituted-1H-benzimidazole derivatives. The reaction was performed in water under ultrasound irradiation, using BiOCl nanoparticles as a catalyst. The nanocatalyst was found to be reusable for seven subsequent reactions without much loss in activity. Simple methodology with short reaction times and mild reaction conditions with easy work-up procedure are the salient features of this method.
- Sapkal, Bharatkumar M.,Labhane, Prakash K.,Satam, Jitendra R.
-
p. 4967 - 4979
(2017/07/22)
-
- Introduction of taurine (2-aminoethanesulfonic acid) as a green bio-organic catalyst for the promotion of organic reactions under green conditions
-
Taurine (2-aminoethanesulfonic acid), a semi-essential amino acid that exists in the human body and numerous other living creatures, is used as a green bio-organic catalyst for the promotion of the Knoevenagel reaction between aldehydes and malononitrile. In the same way, tetraketones can also be produced through a Knoevenagel reaction, followed by Michael addition. 2-Amino-3-cyano-4H-pyran derivatives are simply prepared via a three-component reaction in the presence of taurine as the catalyst. All these reactions are performed in water, a green solvent. The advantages of using of taurine as the catalyst are it is environmentally friendly, low cost, commercially available, easy to separate from the reaction mixture, and has high reusability. Use of this catalyst results in acceptable reaction times, high yields and high purities of the obtained products without utilizing any organic solvents.
- Shirini, Farhad,Daneshvar, Nader
-
p. 110190 - 110205
(2016/11/30)
-
- Nano Fe/NaY zeolite: An efficient and reusable solid-supported catalyst for synthesis of 1-oxo-hexahydroxanthene and tetraketone derivatives
-
Nano Fe/NaY zeolite with high loading of Fe ions was successfully synthesized by the ion-exchange technique at ambient temperature. The prepared Fe/NaY was characterized by X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy, Brunauer-Emmett-Teller (BET) surface area measurements, and Fourier-transform infrared (FT-IR) spectroscopy. The data analyses confirm the presence of iron oxide (up to 32.8 %) with average diameter of 30-40 nm on the surface of NaY zeolite. The catalytic activity of nano Fe/NaY zeolite was examined in the preparation of 1-oxo-hexahydroxanthene and tetraketone derivatives. The results showed its applicability as a green, reusable, and promising catalyst for organic synthesis. This protocol demonstrates several notable advantages including short reaction times, environmentally friendly conditions, no necessity for extraction or chromatographic purification steps, more convenient workup, high yields of products, and lack of use of any injurious solvents. The catalyst was recovered and reused up to four consecutive times without significant loss in catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]
- Tajbakhsh, Mahmood,Heidary, Marzieh,Hosseinzadeh, Rahman
-
p. 1425 - 1439
(2016/04/26)
-
- Method for catalytically synthesizing xanthenedione compound open ring derivatives through hydroxyl ammonium ionic liquid
-
The invention discloses a method for catalytically synthesizing xanthenedione compound open ring derivatives through hydroxyl ammonium ionic liquid, and belongs to the technical field of green synthesis of fine chemicals. According to the technical scheme
- -
-
Paragraph 0018; 0019
(2017/02/02)
-
- An Efficient One-Pot Two-Step Three-Component Process for the Synthesis of Trifluoromethylated Hydrochromenes
-
A one-pot two-step three-component process for the synthesis of trifluoromethylated 2-hydroxy-5-oxo-3,4,5,6,7,8-hexahydro-2H-chromenes has been developed. The three-component reaction of dimedone, substituted benzaldehydes, and methyl 4,4,4-trifluorobut-2-ynoate gave the desired products in moderate to good yields. Excellent regioselectivity and diastereoselectivity were observed. Furthermore, refluxing the product chromenes with p-toluenesulfonic acid in toluene gave the corresponding dehydrated products - trifluoromethylated 5-oxo-5,6,7,8-tetrahydro-4H-chromenes.
- Yan, Xufeng,Yang, Yeqing,Han, Jing,Jiang, Guimei,Chen, Jie,Deng, Hongmei,Shao, Min,Zhang, Hui,Cao, Weiguo
-
supporting information
p. 2863 - 2872
(2016/08/31)
-
- Novel heterogeneous catalyst systems based on Pd(0) nanoparticles onto amine functionalized silica-cellulose substrates [Pd(0)-EDA/SCs]: Synthesis, characterization and catalytic activity toward C-C and C-S coupling reactions in water under limiting basic conditions
-
Novel heterogeneous catalyst systems based on the immobilization of Pd(0) nanoparticles onto ethylene diamine functionalized silica-cellulose substrates [Pd(0)-EDA/SCs] are reported with a view to introduce new synthetic routes under base-free conditions. The base functionalized organic/inorganic hybrid provides specific basic sites for the reactions to occur under base-free or less basic conditions, and that too with excellent yields. Moreover, the basic nitrogen sites present on the substrate can effectively stabilize and enhance the activity of Pd(0) nanoparticles by preventing their agglomeration and controlling their size. All the catalysts were characterized by TGA and FTIR analysis and the most active catalyst, [Pd(0)-EDA/SC-2] was further characterized by SEM, TEM, HRTEM, EDX, CHN and XRD studies. Additionally, it is shown that the Pd(0)-EDA/SCs exhibits excellent activity under limiting basic conditions for the C-C and C-S coupling reactions employing water as the "Green solvent". Furthermore, the novel catalyst could be recovered in a facile manner from the reaction mixture and could be reused up to five times without significant loss of catalytic activity.
- Bhardwaj, Madhvi,Sahi, Seema,Mahajan, Hitesh,Paul, Satya,Clark, James. H.
-
-
- Rapid one pot synthesis of xanthene derivatives by an efficient and reusable nano-ZnAl2O4 - An insight into a new process
-
Nano-ZnAl2O4 was synthesized by blending metal-citrate complex-acrylamide polymer using the precursor method. Powder X-ray diffraction analysis of the catalyst affirmed that the spinel oxide was phase pure. Elemental analysis was confirmed by Energy Dispersive X-ray analysis. Transmission Electron Microscopic (TEM) analysis and Scherrer's formula revealed that the particles were found to be in the order of 20 nm in size. Thermal stability of the catalyst was analyzed by thermogravimetric and differential thermal analysis (TG-DTA). Total acidity of the nano-ZnAl 2O4 evaluated by NH3-TPD was 8.8 mmol NH 3/g. Diversity in the synthesis of xanthene derivatives was investigated using nanozinc aluminate as a catalyst. Nanoform of the catalyst showed better activity than the bulk form due to its large surface area 50 m2/g. The 2,2′-arylmethylene bis (3-hydroxy-2-cyclohexene-1- one), 2,2′-arylmethylene bis (3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) and 1-Oxo-hexahydroxanthenes were synthesized rapidly using ZnAl 2O4 and the catalyst was successfully recycled without any loss of activity.
- Mandlimath, Triveni Rajashekhar,Umamahesh, Balijapalli,Sathiyanarayanan, Kulathu I.
-
p. 198 - 207
(2014/06/10)
-
- Zinc chloride catalyzed collective synthesis of arylmethylene bis(3-hydroxy-2-cyclohexene-1-ones) and 1,8-dioxo-octahydroxanthene/acridine derivatives
-
Catalytic amount of ZnCl2 efficiently promoted rapid synthesis of arylmethylene bis(3-hydroxy-2-cyclohexene-1-one) in water at room temperature in excellent yield. At elevated temperature, ZnCl2 also catalyzed one-pot synthesis of 1,8-dioxo-octahydroxanthene and 1,8-dioxo-decahydroacridine derivatives in good yield. In specific instances, unusual dissociation of dimedone from the arylmethylene bis(3-hydroxy-2-cyclohexene-1-one) was identified in the reaction medium. It was minimized/avoided by the addition of known excess dimedone to the reaction mixture in the one-pot synthesis of 1,8-dioxo-octahydroxanthene.
- Ganesan, Subramaniapillai Selva,Kothandapani, Jagatheeswaran,Ganesan, Asaithampi
-
supporting information
p. 682 - 687
(2015/04/14)
-
- Simple and cost effective acid catalysts for efficient synthesis of 9-aryl-1,8-dioxooctahydroxanthene
-
CaCl2 (20 mol %) dispersion in DMSO or aq HBr (10 mol %) is developed as an efficient and cost effective acid catalyst for the simple one-pot synthesis of 9-aryl-1,8-dioxooctahydroxanthene derivatives. Reaction of aromatic aldehyde (1 equiv) an
- Ilangovan,Muralidharan,Sakthivel,Malayappasamy,Karuppusamy,Kaushik
-
supporting information
p. 491 - 494
(2013/02/23)
-
- Nickel nanoparticles: A highly efficient catalyst for one pot synthesis of tetraketones and biscoumarins
-
A novel and practically useful protocol has been designed wherein, polyvinyl pyrrolidone (PVP) stabilized nickel nanoparticles have been used as a catalyst for promoting the synthesis of 2,2'-aryl-methylene bis(3-hydroxy-5,5- dimethyl-2-cyclohexene-1-one)
- Khurana, Jitender M.,Vij, Kanika
-
p. 907 - 912,6
(2020/09/09)
-
- Eco-friendly synthesis of 1,8-dioxo-octahydroxanthenes catalyzed by ionic liquid in aqueous media
-
A biodegradable functionalized ionic liquid 3-(N,N-dimethyldodecylammonium) propanesulfonic acid hydrogen sulfate ([DDPA][HSO4]) was prepared and used as a Bronsted acid-surfactant-combined catalyst for the eco-friendly one-pot synthesis of 1,8-dioxo-octahydroxanthenes at 100°C in water. Under these conditions, the reaction of various aromatic aldehydes with dimedone generated 1,8-dioxo-octahydroxanthenes in good yields with a simple postreaction procedure. The products could simply be separated from the catalyst/water system, and the catalyst could be reused at least six times without noticeably decreasing the catalytic activity.
- Fang, Dong,Yang, Jin-Ming,Liu, Zu-Liang
-
experimental part
p. 468 - 472
(2011/05/14)
-
- A green and novel method of synthesizing 2,2′-arylmethylene bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) catalyzed by L-histidine in ionic liquid
-
An efficient and green approach to the synthesis of 2,2′- arylmethylene bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) using L-histidine as the catalyst is described. In addition, room temperature ionic liquid 1-butyl-3-methylimidazonium tetrafluoroborate [b
- Zhang, Yan,Shang, Zhicai
-
experimental part
p. 1184 - 1188
(2011/01/12)
-
- Reaction of aldehydes and 5,5-dimethyl-1,3-cyclohexanedione in the presence of surfactants in water
-
An efficient and convenient approach to the synthesis of the two different products from aldehydes and 5,5-dimethyl-1,3-cyclohexanedione using two kinds of surfactant catalysts sodium dodecyl sulfate (SDS) and dodecanesulfonic acid (DSA) (10 mol %) is des
- Qin, Xin-Ying,Jin, Tong-Shou,Zhang, Jian-She,Li, Tong-Shuang
-
experimental part
p. 1173 - 1178
(2012/03/11)
-
- An efficient synthesis of 2,2′-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) and 1,8-dioxooctahydroxanthenes using ZnO and ZnO-acetyl chloride
-
2,2′-Arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) 4l-s produced from reaction between dimedone with various aldehydes in acetonitrile using ZnO as a catalyst; whereas in the presence of ZnO-acetyl chloride catalysts the reaction is limite
- Maghsoodlou, Malek Taher,Habibi-Khorassani, Sayyed Mostafa,Shahkarami, Zahra,Maleki, Nariman,Rostamizadeh, Mohsen
-
experimental part
p. 686 - 689
(2011/10/30)
-
- Bakers' yeast catalyzed synthesis of polyhydroquinoline derivatives via an unsymmetrical Hantzsch reaction
-
Bakers' yeast efficiently catalyzes the unsymmetrical Hantzsch reaction through a four-component coupling of aldehydes, β-ketoesters, dimedone and ammonium acetate to form polyhydroquinoline derivatives in good to excellent yields.
- Kumar, Atul,Maurya, Ram Awatar
-
p. 3887 - 3890
(2008/02/03)
-
- The reaction of aromatic aldehydes and 5,5-dimethyl-1,3-cyclohexanedione under solvent-free grinding conditions
-
The reaction of aromatic aldehyde 1 and 5,5-dimethyl-1,3-cyclohexanedione 2 under solvent-free and solid state conditions has been catalyzed by KF/Al 2O3 or silica sulfate and yields two products: 2,2′-arylmethylene bis(3-hydroxy-5,5
- Jin, Tong-Shou,Wang, Ai-Qing,Ma, Hui,Zhang, Jian-She,Li, Tong-Shuang
-
p. 470 - 474
(2007/10/03)
-
- Solid-state condensation reactions between aldehydes and 5,5-dimethyl-1,3-cyclohexanedione by grinding at room temperature
-
An efficient and convenient approach to the synthesis of the two different products from aldehydes and 5,5-dimethyl-1,3-cyclohexanedione in the solid state by grinding is described. This method provides several advantages such as environmental friendlines
- Jin, Tong-Shou,Zhang, Jian-She,Wang, Ai-Qing,Li, Tong-Shuang
-
p. 2339 - 2345
(2007/10/03)
-
- Solvent-free Knoevenagel condensations and Michael additions in the solid state and in the melt with quantitative yield
-
Numerous Knoevenagel condensations of solid or liquid aromatic aldehydes are performed with four barbituric acids, Meldrum's acid, dimedone, cyanoacetamide, malodinitrile and methyl cyanoacetate in stoichiometric mixtures of the solids or of stoichiometri
- Kaupp, Gerd,Naimi-Jamal, M. Reza,Schmeyers, Jens
-
p. 3753 - 3760
(2007/10/03)
-
- Condensation of aromatic aldehydes with acidic methylene compounds without catalyst
-
The condensation of aromatic aldehyde with isopropylidene malonate or 5,5-dimethyl-1,3-cyclohexanedione is carried out in DMF as solvent without catalyst.
- Shi, Daqing,Wang, Yucheng,Lu, Zaisheng,Dai, Guiyuan
-
p. 713 - 726
(2007/10/03)
-
- CHLOROSULFONATION OF 9-ARYL 3,3,6,6-TETRAMETHYLOCTAHYDROXANTHEN-1,8-DIONES
-
The 9-aryl-3,3,6,6-tetramethyloctahydroxanthendiones (4-20) react with chlorosulfonic acid to give the sulfonyl chlorides (25, 34, 43, 53, 55, 59, 63, and 65).The xanthendione (7) from m-anisaldehyde afforded the bis-sulfonyl chloride (30).The products we
- Cremlyn, Richard J.,Saunders, David
-
-
- Chemistry of dimedone--Structures of aldehyde-dimedone adducts
-
Novel features in the structures and stability of products of the hoary reaction of aldehydes with dimedone are described.Dimedone and cinnamaldehyde afford the bisdimedonyl derivative 3 or the perhydrochroman 5, while 4-dimethylaminocinnamaldehyde afford
- Nagarajan, K,Shenoy, S J
-
-