- A green protocol for Erlenmeyer-Pl?chl reaction by using iron oxide nanoparticles under ultra sonic irradiation
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Azlactones have been prepared via Erlenmeyer synthesis from aromatic aldehydes and hippuric acid using Fe2O3 nanoparticles under ultrasonic irradiation. Short reaction times, easy and quick isolation of the products, and excellent yi
- Ahmadi, Seyed Javad,Sadjadi, Sodeh,Hosseinpour, Morteza
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- Zeolite (Y-H)-based green synthesis, antimicrobial activity, and molecular docking studies of imidazole bearing oxydibenzene hybrid molecules
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In this green synthesis, zeolite (Y-H) appears to be an intriguing choice for obtaining a high yield with a shorter reaction time. In addition, we have synthesized N-aryl-(4-benzylidene-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-3-phenoxybenzamides (4a-i), which will be proved to be potent antimicrobial agents. The title compounds were tested against Gram-positive, Gram-negative, and fungal strains using the Mueller–Hinton Broth technique. N-(4-benzylidene-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-3-phenoxybenzamide (4a) (minimum inhibitory concentration [MIC]?=?25 μg/mL, S. pyogenes) and N-(4-[4-fluorobenzylidene]-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-3-phenoxybenzamide (4f) (MIC?=?100 μg/mL, C. albicans, A. niger, A. clavatus) were the most effective against Gram-positive and Gram-negative bacteria as well as fungal strains. To understand the mechanism of action of synthesized compounds, molecular docking experiments were performed against S. aureus tyrosyl-tRNA synthetase and C. albicans sterol 14-α demethylase.
- Ahmad, Iqrar,Desai, Nisheeth C.,Jethawa, Aratiba M.,Maheta, Abhay S.,Pandit, Unnat P.,Patel, Harun
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supporting information
(2021/12/23)
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- Novel diamide-based benzenesulfonamides as selective carbonic anhydrase ix inhibitors endowed with antitumor activity: Synthesis, biological evaluation and in silico insights
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In this work, we present the synthesis and biological evaluation of novel series of diamide-based benzenesulfonamides 5a-h as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I, II, IX and XII. The target tumor-associated i
- Abdelrahman, Mohamed A.,Eldehna, Wagdy M.,Nocentini, Alessio,Bua, Silvia,Al-Rashood, Sara T.,Hassan, Ghada S.,Bonardi, Alessandro,Almehizia, Abdulrahman A.,Alkahtani, Hamad M.,Alharbi, Amal,Gratteri, Paola,Supuran, Claudiu T.
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- Greener approach: Ionic liquid [Et3NH][HSO4]-catalyzed multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)oxazolones under solvent-free condition
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We have developed simple, greener, safer multicomponent synthesis series of 4-arylidene-2-phenyl-5(4H) oxazolones 4(a-r) catalyzed by Bronsted acid ionic liquid as triethylammonium hydrogen sulfate [Et3NH][HSO4] and catalytic amount of acetic anhydride and sodium acetate with excellent yields (90–99%). The protocol offers economical, environmentally benign, solvent-free conditions, and recycle–reuse of the catalyst and easily available starting as benzoyl chloride 1, amino acid 2 and a variety of aldehydes 3. The cyclization followed by condensation of benzoyl chloride, amino acid, and a variety of aldehydes catalyzed by ILs [Et3NH][HSO4] and catalytic amount of acetic anhydride and sodium acetate. The final products were confirmed by their characterization data such as FTIR, 1H-NMR, 13C-NMR, Mass, high-resolution mass spectra and were compared with its reported method.
- Jadhav, Santosh A.,Sarkate, Aniket P.,Farooqui, Mazahar,Shinde, Devanand B.
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p. 1676 - 1683
(2017/09/08)
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- Microwave-assisted efficient synthesis of azlactones using zeolite NaY as a reusable heterogeneous catalyst
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The efficient preparation of azlactones in the presence of zeolite NaY has been reported. This heterogeneous catalyst was used for efficient synthesis of azlactone derivatives with Ac2O as a condensing agent under microwave irradiation and solvent-free co
- Bodaghifard, Mohammad Ali,Moghanian, Hassan,Mobinikhaledi, Akbar,Esmaeilzadeh, Fatemeh
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p. 845 - 849
(2017/08/10)
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- Synthesis and insecticidal evaluation of tetrahydroimidazo[1,2-a]pyridin-5(1H)-one derivatives
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A series of novel tetrahydroimidazo[1,2-a]pyridine-5(1H)-one derivatives containing a electronegative pharmacophore (=CNO2) were synthesized via practical aza-ene reaction and characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. Preliminary bioassays showed that some of the target compounds exhibited good insecticidal activity against brown planthopper (Nilaparvata lugens) and cowpea aphids (Aphis craccivora) at 500 mg L-1. Among them, compound 11h was active against brown planthopper at 100 mg L-1. The insecticidal activities varied significantly depending on the types and patterns of the substituents, which provided guidance for further investigation on structure modifications.
- Liu, Xuan-Qi,Liu, Ya-Qin,Shao, Xu-Sheng,Xu, Zhi-Ping,Xu, Xiao-Yong,Li, Zhong
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- An innovation for development of Erlenmeyer-Pl?chl reaction and synthesis of AT-130 analogous: A new application of continuous-flow method
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The development of eco-friendly and efficient processes via one-pot multicomponent synthesis is a very attractive topic. In this work, the Erlenmeyer-Pl?chl azlactone synthesis was carried out through unique, safe, fast and practical conditions without any catalyst, applying a simple microreactor and gave the corresponding products exclusively. A continuous, first microflow synthesis of N-benzoylglycine carbamide derivatives as AT-130 analogues catalyzed by Nafion-H@SPIONs was also established successfully.
- Shafiee, Behnaz,Hadian, Laleh,Khosropour, Ahmad R.
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p. 19861 - 19866
(2016/03/04)
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- An expedient synthesis of oxazolones using a cellulose supported ionic liquid phase catalyst
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A novel cellulose supported ionic liquid phase catalyst containing hydroxide ions ([CellFemImi]OH) has been synthesized by covalent anchoring of 1-N-ferrocenylmethyl imidazole in the functionalized cellulose matrix followed by an anion metathesis reaction. The [CellFemImi]OH was characterized by various techniques including FT-IR, FT-Raman, 13C solid state NMR, X-ray diffraction, energy dispersive X-ray (EDX) analysis, field emission scanning electron microscopy (FESEM) and thermogravimetric analysis. The [CellFemImi]OH was effectively employed as a heterogeneous catalyst in the synthesis of oxazolones by cyclocondensation of aryl aldehydes with hippuric acid in the presence of acetic anhydride.
- Kurane, Rajanikant,Khanapure, Sharanabasappa,Kale, Dolly,Salunkhe, Rajashri,Rashinkar, Gajanan
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p. 44135 - 44144
(2016/06/09)
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- Microwave-assisted efficient and mild synthesis of azlactone derivatives
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(Formula presented) A convenient and mild procedure for the synthesis of azlactones in the presence of catalytic amounts of calcium hydrogen phosphate as a green, inexpensive and environmentally benign catalyst has been demonstrated. The present protocol is operationally simple and offers some advantages such as good yields, short reaction time, simple work-up, low cost and reusability of catalyst, which makes this method mild and eco-friendly.
- Bodaghifard, Mohammad Ali,Mobinikhaledi, Akbar,Moradi, Khosro
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p. 193 - 197
(2016/07/15)
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- Synthesis and quantitative structure-activity relationships study for phenylpropenamide derivatives as inhibitors of hepatitis B virus replication
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A series of new phenylpropenamide derivatives containing different substituents was synthesized, characterized and evaluated for their anti-hepatitis B virus (HBV) activities. The quantitative structure eactivity relationships (QSAR) of phenylpropenamide compound have been studied. The 2D-QSAR models, based on DFT and multiple linear regression analysis methods, revealed that higher values of total energy (TE) and lower entropy (Sθ) enhanced the anti-HBV activities of the phenylpropenamide molecules. Predictive 3D-QSAR models were established using SYBYL multifit molecular alignment rule. The optimum models were all statistically significant with cross-validated and conventional coefficients, indicating that they were reliable enough for activity prediction.
- Yang, Jing,Ma, Min,Wang, Xue-Ding,Jiang, Xing-Jun,Zhang, Yuan-Yuan,Yang, Wei-Qing,Li, Zi-Cheng,Wang, Xi-Hong,Yang, Bin,Ma, Meng-Lin
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- Nanocrystalline titanium dioxide catalyst for the synthesis of azlactones
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Titanium dioxide nanoparticles were prepared by a electrochemical reduction method using parameters such as current density, solvent polarity, distance between electrodes, and concentration of stabilizers to control the size of the nanoparticles. The nanoparticles were characterized by UV-Vis spectroscopy, X-ray diffraction, scanning electron microscopy and transmission electron microscopy, and their catalytic performance was tested for the synthesis of a series of 4-aryldiene-2-phenyl-5(4)-oxazolones from the cyclodehydration and condensation of the respective aldehyde, hippuric acid and acetic anhydride. Easy availability, reusability and eco-friendliness were some prominent features of the nanocrystalline titanium dioxide catalyst.
- Anandgaonker, Priyanka,Kulkarni, Ganesh,Gaikwad, Suresh,Rajbhoj, Anjali
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p. 196 - 200
(2014/03/21)
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- Facile synthesis of 4-arylidene-5-imidazolinones as synthetic analogs of fluorescent protein chromophore
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A facile and effective synthesis for a wide variety of 4-arylidene-5- imidazolinone derivatives was developed. 4-Arylidene-5-oxazolinones were prepared by Erlenmeyer azlactone synthesis from N-acylglycines and arylaldehydes. The ring-opening reactions of the 4-arylidene-5-oxazolinones with primary amines afforded 2-acylamino-3-arylacrylamides in excellent yields. A new dehydrative cyclization of the 2-acylamino-3-arylacrylamides in pyridine under reflux furnished the corresponding 4-arylidene-5-imidazolinones in good yields.
- Lee, Cheng-Yu,Chen, Yun-Chung,Lin, Hao-Chun,Jhong, Yuandong,Chang, Chih-Wei,Tsai, Ching-Hua,Kao, Chai-Lin,Chien, Tun-Cheng
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supporting information; experimental part
p. 5898 - 5907
(2012/09/07)
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- Construction of adjacent spiro-quaternary and tertiary stereocenters through phosphine-catalyzed asymmetric [3+2] annulation of allenoates with alkylidene azlactones
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A novel axially chiral spiro-phosphine-catalyzed highly regio-, diastereo- and enantioselective [3+2] cycloaddition of alkylidene azlactones with various allenic esters has been developed, affording the corresponding functionalized spirocyclic products in
- Wang, De,Wei, Yin,Shi, Min
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supporting information; experimental part
p. 2764 - 2766
(2012/04/05)
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- Novel and chemoselective one-pot synthesis of 4-arylidene-2-phenyl-5(4H)- oxazolones starting from benzyl alcohols promoted by [(C14H 24N4)2W10O32]-[bmim] NO3
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A new and practical promoter system for one-pot, efficient, chemoselective synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones using [(C14H 24N4)2W10O32]-[bmim] NO3 under solvent-free conditions is described. The present work opens up a new and ecofriendly synthetic route to Erlenmeyer-Ploechl adducts from primary benzyl alcohols in a one-pot operation. Graphical abstract: [Figure not available: see fulltext.]
- Rostami, Mahboubeh,Khosropour, Ahmad Reza,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj,Moghadam, Majid,Tangestaninejad, Shahram
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experimental part
p. 1175 - 1180
(2012/01/06)
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- 2W10O32. 2H2O: A novel and powerful catalyst for the synthesis of 4-arylidene-2-phenyl-5(4)-oxazolones under ultrasonic condition
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Di[1,6-bis(3-methylimidazolium-1-yl)hexane] decatungstate dihydrate ([C6(MIm)2]2W10O32. 2H2O) as a new family of polyoxometalate-based dicationic ionic liquids (POM-DIL) is synthesized and employed as a novel and powerful heterogeneous catalyst in the synthesis of 4-arylidene-2-phenyl-5(4)-oxazolones (azlactones) under ultrasound-assisted solvent-free condition. On the basis of the results, the products were obtained in excellent yields under mild condition. Utilization of easy work-up and purification make it very interesting from an economic perspective. Moreover, a recycling study confirmed that the catalyst can be reused multiple times without significant loss of its activity.
- Rostami, Mahboubeh,Khosropour, Ahmad R.,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj,Moghadam, Majid,Tangestaninejad, Shahram
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experimental part
p. 869 - 877
(2012/04/23)
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- New and convenient route for the synthesis of some new pyrazol-5-yl-1H- imidazole derivatives
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A simple and efficient method for the synthesis of some new pyrazol-5-yl-1H-imidazoles 4a-h is described. In this method oxazolones 5a-h were produced as minor products. The X-ray analysis confirmed the structures of 4 and 5. The Japan Institute of Heterocyclic Chemistry.
- Zonouzi, Afsaneh,Mirzazadeh, Roghieh,Talebi, Marzieh,Jafarypoor, Razieh,Peivandi, Azadeh,Ng, Seik Weng
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experimental part
p. 2131 - 2138
(2011/04/18)
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- One-pot process to Z-α-benzoylamino-acrylic acid methyl esters via potassium phosphate-catalyzed Erlenmeyer reaction
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A practical and efficient two reaction sequence one-pot process for the synthesis of Z-α-benzoylamino-acrylic acid methyl esters was developed. The process involves a potassium phosphate-catalyzed Erlenmeyer reaction of aromatic aldehydes with hippuric acid followed by an oxazolone ring-opening methanolysis. This process afforded a good overall yield and an excellent product quality via a simple workup.
- Cleary, Thomas,Brice, Jodie,Kennedy, Nicole,Chavez, Flavio
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supporting information; experimental part
p. 625 - 628
(2010/04/05)
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- Catalyzing the Erlenmeyer Pl?chl reaction: organic bases versus sodium acetate
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An evaluation of organic base versus sodium acetate as the base in the Erlenmeyer Pl?chl reaction was performed. Aldehyde substituents play an important role in these reactions. Organic bases afford fast reactions, but other side reactions were observed. Alternatively, in the presence of solvent, sodium acetate could be used in catalytic amounts rather than the typical stoichiometric quantities. This Letter reports the comparative results for the use of organic bases versus sodium acetate in Erlenmeyer Pl?chl reactions.
- Cleary, Thomas,Rawalpally, Thimma,Kennedy, Nicole,Chavez, Flavio
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supporting information; experimental part
p. 1533 - 1536
(2010/06/13)
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- An efficient synthesis of new class of pyrazolo[3,4-b]pyridine-6-one derivatives by a novel cascade reaction
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(Chemical Equation Presented) A novel cascade reaction of 4-arylidene-2-phenyl-1,3-oxazol-5(4H)-one with 3-methyl-l-phenyl-1H-pyrazol-5- amine was described and a number of new pyrazolo[3,4-b]pyridine-6-one derivatives were synthesized. This new protocol has the advantages of shorter time, higher yields, and lower cost as well as easier operation.
- Shi, Feng,Zhang, Junyong,Tu, Shujiang,Jia, Runhong,Zhang, Yan,Jiang, Bo,Jiang, Hong
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p. 1013 - 1017
(2008/03/29)
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