- Synthesis and in vitro carbonic anhydrases and acetylcholinesterase inhibitory activities of novel imidazolinone-based benzenesulfonamides
-
New imidazolinone-based benzenesulfonamides 3a–e and 4a–e were synthesized in three steps?and their chemical structures were confirmed by 1H NMR (nuclear magnetic resonance), 13C NMR, and high-resolution mass spectrometry. The benzenesulfonamides used were sulfacetamide (3a, 4a), sulfaguanidine (3b, 4b), sulfanilamide (3c, 4c), sulfadiazine (3d, 4d), sulfamerazine (3e), and sulfathiazole (4e). The compounds were evaluated against carbonic anhydrase (CA) and acetylcholinesterase (AChE) enzymes to obtain possible drug candidate/s. The lead compounds of the series were 3a and 4a against human CA (hCA) I, whereas?3d and 4a were leads against hCA II in terms of Ki values. Series 4 includes more effective CAs inhibitors than series 3 (except 3d). Series 4 compounds having a nitro group (except 4d) were 3.3–4.8 times more selective inhibitors than their corresponding analogues 3a–d in series 3, in which hydrogen was located in place of the nitro group, by considering Ki values against hCA II. Compounds 3c and 4c, where the sulfanilamide moiety is available, were the leads in terms of AChE inhibition with the lowest Ki values. The use of secondary sulfonamides was a more effective modification on CA inhibition, whereas the primary sulfonamide was the effective substitution in terms of AChE inhibitory potency.
- Tugrak, Mehtap,Gul, Halise Inci,Demir, Yeliz,Levent, Serkan,Gulcin, Ilhami
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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)
-
- Discovery of a necroptosis inhibitor improving dopaminergic neuronal loss after mptp exposure in mice
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Parkinson’s disease (PD) is the second most common neurodegenerative disorder, mainly characterized by motor deficits correlated with progressive dopaminergic neuronal loss in the substantia nigra pars compacta (SN). Necroptosis is a caspase-independent f
- Oliveira, Sara R.,Dionísio, Pedro A.,Gaspar, Maria M.,Ferreira, Maria B. T.,Rodrigues, Catarina A. B.,Pereira, Rita G.,Estev?o, Mónica S.,Perry, Maria J.,Moreira, Rui,Afonso, Carlos A. M.,Amaral, Joana D.,Rodrigues, Cecília M. P.
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- Novel Approach to the Synthesis of 3-amino-4-arylpyridin-2(1H)-one Derivatives
-
[Figure not available: see fulltext.] The reaction of 4-arylidene-2-phenyloxazol-5(4H)-ones with enamines of ethyl acetoacetate gave 4-aryl-2-methyl-6-oxo-5-[(phenylcarbonyl)amino]-1,4,5,6-tetrahydropyridine-3-carboxylic acid esters, which, when heated with phosphorus oxychloride, were converted into esters of 7-aryl-5-methyl-2-phenyloxazolo[5,4-b]pyridine-6-carboxylic acids. Alkaline hydrolysis of these compounds gave 4-aryl-2-methyl-6-oxo-5-[(phenylcarbonyl)amino]-1,6-dihydropyridine-3-carboxylic acid esters.
- Chernenko, Sergei А.,Dmitriev, Maksim V.,Fisyuk, Alexander S.,Samsonenko, Anna L.,Shatsauskas, Anton L.,Shuvalov, Vladislav Yu.
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p. 764 - 771
(2021/10/04)
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- Design and development of 5-(4H)-oxazolones as potential inhibitors of human carbonic anhydrase VA: towards therapeutic management of diabetes and obesity
-
Inhibitors of carbonic anhydrase (CAIs) hold promise for addressing various diseases, including cancer, diabetes, and other metabolic syndromes. CAV is the only isoform present in the mitochondria and is considered a potential drug target for obesity. In
- Alajmi, Mohamed F.,Das Mahapatra, Amarjyoti,Datta, Bhaskar,Hassan, Md. Imtaiyaz,Hussain, Afzal,Khan, Parvez,Queen, Aarfa,Rehman, Md. Tabish,Yousuf, Mohd
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- Synthesis and luminescence properties of analogues of the green fluorescent protein chromophore
-
The green fluorescent protein (GFP) is extensively used as a biomarker for fluorescence biological imaging. The chromophore in GFP is only fluorescent when confined into the β–barrel of the protein. Similarly, synthetic analogues of the fluorophore of GFP
- Esteves, Cátia I. C.,Guieu, Samuel,Rocha, Jo?o,Silva, Artur M. S.,da Silva Fonseca, Inês
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- Synthesis of 2-substituted 4-arylidene-5(4h)-oxazolones as potential cytotoxic agents in the presence of lemon juice as a biocatalyst
-
Background: The oxazolone class of compounds is known to exert a profound effect on malignant cell proliferation, tumor angiogenesis and /or on the established neoplastic vasculature. Additionally, these compounds are generally known to have a low tendenc
- Anand, Krishnan,Jonnalagadda, Sreekantha B.,Katari, Naresh K.,Lakshmi, Chapala V.,Pal, Manojit,Prasad, Malavattu G.
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p. 625 - 634
(2020/01/21)
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- Copper nitrate-mediated synthesis of 3-aryl isoxazolines and isoxazoles from olefinic azlactones
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A copper nitrate-mediated [2 + 2 + 1] cycloaddition reaction was developed for the expedient synthesis of pharmacologically interesting 3-aryl substituted isoxazolines and isoxazoles through CC bond cleavage. Copper nitrate is employed as a reaction promoter and precursor of nitrile oxides. The given approach features a new mode of cycloaddition from olefinic azlactones, copper nitrate and unsaturated compounds with wide substrate scope, good functional group tolerance and operational simplicity.
- Lin, Yifan,Zhang, Ke,Gao, Mingchun,Jiang, Zheyi,Liu, Jiajie,Ma, Yurui,Wang, Haoyu,Tan, Qitao,Xiao, Junjie,Xu, Bin
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supporting information
p. 5509 - 5513
(2019/06/14)
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- An ionic liquid gel: A heterogeneous catalyst for Erlenmeyer-Plochl and Henry reactions
-
An ionic liquid gel has been prepared by entrapping 1-butyl-3-methylimidazolium hydroxide ([Bmim]OH) in an aqueous agar gel. The ionic liquid gel has been characterized by Fourier transform infrared (FT-IR), Fourier transform Raman (FT-Raman) spectroscopy, scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and energy dispersive X-ray analysis (EDX). The ionic liquid gel has been successfully employed as a heterogeneous catalyst in the Erlenmeyer-Plochl reaction involving aldehydes, hippuric acid and acetic anhydride as well as in the Henry reaction between aldehydes and nitromethane in ethanol at room temperature. The heterogeneity of the ionic liquid gel has been confirmed by conducting hot filtration tests and leaching studies. Additionally, the ionic liquid gel could be easily recovered by simple filtration and reused five times without significant loss in catalytic activity.
- Jagadale, Megha,Naikwade, Altafhusen,Salunkhe, Rajashri,Rajmane, Mohan,Rashinkar, Gajanan
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p. 10993 - 11005
(2018/07/06)
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- Sulfanilic acid-catalyzed green synthesis of 4-Arylidene-2-phenyl-5(4H)-Oxazolones
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This study is focused on the catalytic activity of sulfanilic acid (SA) in the straightforward synthesis of 4-Arylidene-2-phenyl-5(4H)-oxazolones via condensation of aromatic aldehydes, hippuric acid, and acetic anhydride under green experimental conditio
- Kiyani, Hamzeh,Aslanpour, Shiva
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p. 297 - 303
(2018/02/22)
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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
-
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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- Synthesis of Erlenmeyer-Pl?chl azlactones promoted by 5-Sulfosalicylic acid
-
5-Sulfosalicylic acid was found as an efficient catalyst in the synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones by condensation and cyclodehydration of aromatic aldehydes with hippuric acid and acetic anhydride at room temperature. The catalyst was eas
- Kiyani, Hamzeh,Aslanpour, Shiva
-
p. 1314 - 1321
(2017/07/18)
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- Triphenylphosphine (PPh3) Catalyzed Erlenmeyer Reaction for Azlactones under Solvent-free Conditions
-
This study presents triphenylphosphine catalyzed process for the synthesis of azlactones and their derivatives using hippuric and substituted aromatic aldehydes. The methodology also found to be effective for the synthesis of azlactones from 5-(2,6-dichlorophenyl)-3-methyl-1,2-oxazol-4-yl carbonyl amino acetic acid and offers several advantages such as solvent-free conditions, excellent yields, simple procedure, mild conditions, and reduced environmental consequences.
- Punna Rao, Alapati Mohan Lakshmi,Sridhar Rao, Abburi,Saratchandra Babu, Mukkamala,Krishnaji Rao
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supporting information
p. 429 - 435
(2017/02/03)
-
- Synthesis and insecticidal evaluation of tetrahydroimidazo[1,2-a]pyridin-5(1H)-one derivatives
-
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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-
- Microwave-Assisted Erlenmeyer Synthesis of Azlactones Catalyzed by MgO/Al2O3 under Solvent-Free Conditions
-
MgO/Al2O3 catalyzes the synthesis of azlactone derivatives from condensation reaction of aldehydes (or ketones) with hippuric acid and acetic anhydride as a dehydrating agent under microwave irradiation. The low toxicity, low cost, ease of handling, and high activity of MgO/Al2O3 make this procedure particularly attractive. Also, this catalyst can be easily recovered by decant and can be reused for this condensation five times in succession without considerable loss of its catalytic activity.
- Rostamizadeh, Nader,Khajeh-Amiri, Alireza,Moghanian, Hassan
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p. 631 - 634
(2015/12/26)
-
- An innovation for development of Erlenmeyer-Pl?chl reaction and synthesis of AT-130 analogous: A new application of continuous-flow method
-
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)
-
- Microwave-assisted efficient and mild synthesis of azlactone derivatives
-
(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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- A convenient synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones under solvent-assisted grinding
-
A facile and effective approach for the synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones has been developed. Under solvent-assisted grinding in the presence of 2,4,6-trichloro-1,3,5-triazine, catalytic triphenylphosphine, and sodium carbonate, dehydrati
- Pattarawarapan, Mookda,Jaita, Subin,Phakhodee, Wong
-
supporting information
p. 3171 - 3174
(2016/07/06)
-
- One flask synthesis of esters of the corresponding 3-substituted 2-benzoylamino acrylic acids using 2-oxazolin-5-ones as synthons
-
A modified route for the fast and facile synthesis of an alkyl 3-substituted 2- benzoylamino acrylate (4) is hereby developed. All the required steps are carried out in the same flask.
- Ahmed, Md. Mizanur,Borthakur, Somadrita,Tripathy, Pradeep K.
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p. 371 - 372
(2019/01/21)
-
- Catalyst-Free and Green Synthesis of Some Novel Benzamide Derivatives
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In the present work, a simple, green, rapid, and catalyst-free procedure for the synthesis of benzamide derivatives by ring opening of azlactones with diamines such as ethylene diamine and 1,3-propylenediamine is described. The present method offers several advantages such as short reaction times, easy work-up, and mild reaction conditions in the absence of catalyst and any toxic solvent and material. In addition, the structure obtained by X-ray crystallography was compared with the theoretical results obtained by density functional theory using the B3LYP functional and cc-pVDZ basis sets.
- Samani Ghaleh Taki, Banafshe,Rostami, Mahbubeh,Mirkhani, Valiollah,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Tangestaninejad, Shahram,Jamali Moghadam, Ahmad,Kia, Reza
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p. 1848 - 1857
(2015/11/09)
-
- [Et3NH][HSO4]-mediated functionalization of hippuric acid: an unprecedented approach to 4-arylidene-2-phenyl-5(4H)-oxazolones
-
A facile, green and stereoselective approach for the synthesis of azlactones/oxazolones 3(a-q) has been developed. The protocol involves reaction of hippuric acid and substituted heterocyclic/aromatic aldehydes in ionic liquid [Et3NH][HSO4] to yield the desired 4-arylidene-2-phenyl-5(4H)-oxazolones in excellent yields (94-97%) with a high degree of purity. The remarkable feature of this pathway is that the ionic liquid eliminates the use of toxic and expensive acetic anhydride and is endowed with catalytic and medium engineering ability. This eco-friendly approach improved synthetic efficiency (94-97% yield), minimizing the production of chemical waste without using highly toxic reagents for the synthesis and more notably, it promoted the selectivity for Z-azlactones/oxazolones. Density functional theory (DFT) calculations revealed that the Z-isomer of compound 3a is stabilised by 2.32 kcal mol-1 more than the E-isomer. This synthetic scheme possesses diverse applicability and is compatible to a range of functional groups (electron donating/electron withdrawing).
- Parveen, Mehtab,Ahmad, Faheem,Malla, Ali Mohammed,Azaz, Shaista,Silva, Manuela Ramos,Silva, P. S. Pereira
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p. 52330 - 52346
(2015/06/25)
-
- Nanocrystalline titanium dioxide catalyst for the synthesis of azlactones
-
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)
-
- Synthesis, characterization and anticonvulsant activity of substituted imidazolinone derivatives
-
The reaction of glycine with benzoylchloride gave 2-benzamidoacetic acid (1) which on reaction with substituted benzaldehydes in presence of acetic anhydride and anhydrous sodium acetate gave 4-benzylidene-2-phenyloxazol-5(4H)-one derivatives (2a-h). 4-Ni
- Sudha, B. Naga,Subbaiah, N. Yella,Raghavendra,Srikanth,Reddy, C.Venkataramana,Manasa
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p. 159 - 162
(2019/01/21)
-
- An efficient and green synthesis of benzylidene-2-N-(carbothioamido)-6-oxo-1,2,5,6-tetrahydro-1-NH-1,2,4-triazine derivatives and their antibacterial activity evaluation
-
An efficient and green synthesis of (Z)-3-allkyl-5(benzylidene/substituted benzylidene)-2N-(carbothioamido)-6-oxo-1,2,5,6-tetrahydro-1-NH-1,2,4-triazine derivatives have been developed in good yields and tested for their antibacterial activities against Escherichia coli, Providencia aeruginosa, Pseudomonas azotogensis and Baccilus subtillis. Some of the synthesized compounds possess good activity against Escherichia coli and Baccilus subtillis compared to standard drug streptomycin.
- Rani, V. Anitha,Kumari, Y. Bharathi
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p. 5931 - 5934
(2015/02/19)
-
- A green protocol for Erlenmeyer-Pl?chl reaction by using iron oxide nanoparticles under ultra sonic irradiation
-
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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p. 408 - 412
(2013/01/15)
-
- Sonochemical hot-spot assisted one-pot synthesis of 4-arylmethylidene-2- phenyl-4H-oxazol-5-ones using nano-mgo as an efficient catalyst
-
Twelve 4-arylmethylidene-2-phenyl-4H-oxazol-5-ones were prepared in excellent yield by sonicating a mixture of an araldehyde, hippuric acid and acetic anhydride in the presence of a green heterogeneous NanoMgO as a basic catalyst. The catalytic activity o
- Saleh Azzam, Sadeq Hamood,Chandrappa,Pasha, Mohamed Afzal
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p. 283 - 290
(2013/07/26)
-
- Oxazolone-based photoswitches: Synthesis and properties
-
The synthesis, photophysics and photochemistry of a family of molecular switches inspired by the green fluorescent protein (GFP) chromophore is presented. These compounds can be synthesized in one step and good yields, their photophysical properties may b
- Blanco-Lomas, Marina,Funes-Ardoiz, Ignacio,Campos, Pedro J.,Sampedro, Diego
-
supporting information
p. 6611 - 6618
(2013/11/06)
-
- Benzylidene-oxazolones as photoswitches: Photochemistry and theoretical calculations
-
The photophysics and photochemistry of a family of compounds proposed as efficient molecular photoswitches is presented. The effect of different light sources, substituents and solvents in the photostationary state has been explored. A detailed mechanisti
- Funes-Ardoiz, Ignacio,Blanco-Lomas, Marina,Campos, Pedro J.,Sampedro, Diego
-
supporting information
p. 9766 - 9771
(2013/10/22)
-
- Ammonium metavanadate an efficient catalyst for Erlenmeyer synthesis
-
An efficient method to synthesize azalactone derivatives using ammonium metavanadate (NH4VO3) as catalyst was performed in the absence of solvent. This method is environmentally friendly and affords the product azalactones in high yi
- Madje, Balaji,Ubale, Milind,Bharad, Jagdish,Shingare, Murlidhar
-
p. 1295 - 1299
(2013/01/15)
-
- Facile synthesis of 4-arylidene-5-imidazolinones as synthetic analogs of fluorescent protein chromophore
-
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
-
supporting information; experimental part
p. 5898 - 5907
(2012/09/07)
-
- Microwave-assisted efficient synthesis of azlactone derivatives using TsCl/DMF under solvent-free conditions
-
A simple and efficient procedure for the synthesis of azlactones employing condensation reaction of aromatic aldehydes with hippuric acid has been developed by using the tosyl chloride (TsCl) and dimethylformamide (DMF) system as condensing agent in the absence of solvents under microwave irradiation. The present protocol is operationally simple and offers several advantages such as high yields, short reaction time, and simple workup.
- Moghanian, Hassan,Shabanian, Meisam,Jafari, Hadi
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experimental part
p. 346 - 349
(2012/06/30)
-
- Construction of adjacent spiro-quaternary and tertiary stereocenters through phosphine-catalyzed asymmetric [3+2] annulation of allenoates with alkylidene azlactones
-
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
-
supporting information; experimental part
p. 2764 - 2766
(2012/04/05)
-
- Two-photon absorption properties of push-pull oxazolones derivatives
-
New fluorescent oxazolone derivatives with high two-photon absorption cross-section were synthesized. Electron donor (phenyl, dimethylaniline and furanyl) and acceptor (nitrobenzene and ethenyl-phenyl-benzimidazol) groups have been appended to the methyle
- Rodrigues, Catarina A.B.,Mariz, Inês F.A.,Ma??as, Ermelinda M.S.,Afonso, Carlos A.M.,Martinho, José M.G.
-
p. 713 - 722
(2012/11/06)
-
- Diastereoselective synthesis of 5-iminooxazolines and their subsequent transformation to α,α-disubstituted dipeptide esters: A formal [4+1] cycloaddition reaction of cyclohexyl isocyanide and Z-alkyl-α-benzoyl amino-acrylates
-
A novel atom economical diastereoselective synthesis of 5-iminooxazolines and their subsequent transformation to α,α-disubstituted dipeptide esters is described. Heating a mixture of cyclohexyl isocyanide and Z-α-benzoyl amino-acrylic acid alkyl esters un
- Esmaeili, Abbas Ali,Shahmansouri, Shima,Habibi, Azizollah,Fakhari, Ali Reza
-
scheme or table
p. 8046 - 8051
(2012/10/07)
-
- 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
-
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
-
experimental part
p. 1175 - 1180
(2012/01/06)
-
- 2W10O32. 2H2O: A novel and powerful catalyst for the synthesis of 4-arylidene-2-phenyl-5(4)-oxazolones under ultrasonic condition
-
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
-
experimental part
p. 869 - 877
(2012/04/23)
-
- Organic-inorganic hybrid polyoxometalates: Efficient, heterogeneous and reusable catalysts for solvent-free synthesis of azlactones
-
Two organic-inorganic hybrid polyoxometalates, consist of 1-butyl-3-methylimidazolium salts of (W10O32)4- and (PW12O40)3- polyanions were prepared and characterized by thermal analysis, X-ray diffraction, FT-IR, diffuse reflectance UV-Vis spectroscopic methods and nitrogen absorption-desorption determination (BET). These heterogeneous catalysts were used for synthesis of azlactones by the reaction of aldehydes with hippuric acid and acetic anhydride under solvent-free conditions. These catalysts were reused several times without loss of their activities.
- Rostami, Mahbubeh,Khosropour, Ahmadreza,Mirkhani, Valiollah,Moghadam, Majid,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj
-
experimental part
p. 27 - 34
(2012/01/03)
-
- Palladium-catalyzed diastereo- and enantioselective synthesis of substituted cyclopentanes through a dynamic kinetic asymmetric formal [3+2]-cycloaddition of vinyl cyclopropanes and alkylidene azlactones
-
An enantioselective preparation of vinylcyclopentanes has been achieved through the title reaction (see scheme). A range of aryl, heterocyclic, alkenyl, and alkyl substituted azlactone alkylidenes have been utilized, giving the cyclopentane products in go
- Trost, Barry M.,Morris, Patrick J.
-
supporting information; experimental part
p. 6167 - 6170
(2011/08/22)
-
- Alum an efficient catalyst for erlenmeyer synthesis
-
A new and efficient method to synthesize azlactone derivatives using alum ascatalyst was performed in the absence of additional solvent. This method is environmentally friendly and affords the product azlactones in high yields after simple workup.
- Madje, Balaji R.,Ubale, Milind B.,Bharad, Jagdish V.,Shingare, Murlidhar S.
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experimental part
p. 158 - 161
(2012/01/06)
-
- 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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- Molecular iodine-catalyzed, mild, effective, ecofriendly, microwave-assisted, one-pot synthesis of 5-arylmethylidene-2-phenyloxazol-4-ones (Azalactones) under solvent-free conditions
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Fourteen azalactones have been synthesized in excellent yields under solvent-free conditions by heating an aldehyde, hippuric acid, and acetic anhydride in the presence of molecular iodine as a catalyst in a microwave oven. The short reaction time, cleaner reaction, and easy workup make this protocol practical and economically attractive. Copyright
- Reddy, M. B. Madhusudana,Pasha
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experimental part
p. 1895 - 1898
(2010/09/07)
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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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- Substituents effect on the erlenmeyer-ploechl reaction: Understanding an observed process reaction time
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A systematic study on hippuric acid substituents was performed in order to better understand the influence of stereoelectronic factors on the Erlenmeyer reaction rate. In addition, two reaction systems were evaluated: Huenig's base solvent free conditions and catalytic sodium acetate in 2-methyl-THF. The effect on reaction rate of electron withdrawing and electron donating groups are reported. Specifically, the study led to the conclusion that stereoelectronic factors have significant influence in one of our key Erlenmeyer reaction by affecting its reaction rate.
- Chavez, Flavio,Kennedy, Nicole,Rawalpally, Thimma,Williamson, R. Thomas,Cleary, Thomas
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experimental part
p. 579 - 584
(2011/07/08)
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- Synthesis and evaluation of substituted imidazolones for antiinflammatory and antioxidant activities
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A series of 4-substituted benzylidene-2-phenyl-1-substituted phenyl-1H-imidazol-5(4H)-one were synthesized by condensation of substituted oxazolones with p-amino benzoic acid and benzocaine. The chemical structures of synthesized compounds were confirmed
- Sarala Devi,Rajitha,Bharathi
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scheme or table
p. 5271 - 5276
(2012/07/28)
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- A new, efficient and chemoselective one-pot protocol for synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones from aryl aldehyde bisulfite adducts promoted by POCl3
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(Chemical Equation Presented) A one-pot procedure for the synthesis of 4-arylidene-2-phenyl-5(4H)oxazolones directly from aryl aldehyde bisulfite adducts in the absence of Ac2O in good to excellent yields using phosphoryl chloride is reported. In addition, the observed chemoselectivity can be considered as a noteworthy advantage of this method.
- Khosropour, Ahmad R.,Khodaei, Mohammad M.,Hoseini Jomor, Seyed J.
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p. 683 - 686
(2008/09/21)
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- Synthesis and pharmacological evaluation of imidazole derivatives of some non-steroidal anti-inflammatory drugs
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A series of imidazole derivatives of NSAIDs (4a-l) have been prepared by condensation of NSAIDs hydrazides (1,2) with substituted oxazolones and evaluated for anti-inflammatory and gastrointestinal toxicity, which showed good anti-inflammatory activity and reduced gastrointestinal toxicity as compared to parent drug.
- Parcha, Versha,Kaur, Jaswinder,Gupta, Vinay,Anroop
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experimental part
p. 321 - 325
(2009/06/25)
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- Erlenmeyer synthesis for azlactones catalyzed by ytterbium(III) triflate under solvent-free conditions
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A series of 4-arylidene-2-phenyl-5(4)-oxazolones were synthesized from cyclodehydration-condensation of hippuric acid, aromatic aldehydes, and acetic anhydride catalyzed by ytterbium(III) triflate under mild conditions in excellent yields. Copyright Taylo
- Yu, Chuanming,Zhou, Baocheng,Su, Weike,Xu, Zhenyuan
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p. 3447 - 3453
(2007/10/03)
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- Montmorillonite K-10 mediated Erlenmeyer synthesis of 4-arylmethylene-2- phenyl-5(4H)-oxazolones
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Aromatic aldehydes and hippuric acid in acetic anhydride undergoes classical Erlenmeyer synthesis in the presence of a catalytic amount of Montmorillonite K-10 to afford the corresponding azlactones in excellent yields with high selectivity. The azlactone
- Karade,Shirodkar,Dhoot,Waghmare
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- Synthesis and immunomodulatory properties of selected oxazolone derivatives
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Eleven oxazolone derivatives were synthesized and characterized by 1H NMR, EI, IR and UV spectroscopic and CHN analysis. Three compounds, 4-[(E)-(4-nitrophenyl)methylidene]-2-phenyl-1,3-oxazol-5(4H)-one (11), 4-[(E)-(4-methoxyphenyl)methylidene]-2-methyl-1,3-oxazol-5-one (12) and 4-[(E)-(4-nitrophenyl)methylidene]-2-methyl-1,3-oxazol-5(4H)-one (13) were screened for phagocyte chemiluminescence, neutrophil chemotaxis, T-cell proliferation, cytokine production from mononuclear cells and cytotoxicity. 4-[(E)-(4-Nitrophenyl)methylidene]-2-methyl-1,3-oxazol-5(4H)-one (13) was found to be the most potent immunomodulator in the series.
- Mesaik, Muhammad A.,Rahat, Shagufta,Khan, Khalid M.,Zia-Ullah,Choudhary, Muhammad I.,Murad, Shahnaz,Ismail, Zakiah,Atta-ur-Rahman,Ahmad, Aqeel
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p. 2049 - 2057
(2007/10/03)
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- Solid support Erlenmeyer synthesis of azlactones using microwaves
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A rapid and efficient protocol for the synthesis of azlactones is reported starting from acetyl/benzoylglycine and various aromatic aldehydes in the presence of acetic anhydride and sodium acetate in dry media using silica gel as solid support under microwave irradiation. The mild conditions, excellent yields, high purity. short reaction time and easy work-up are some of the major advantages of this method.
- Mogilaiah,Prashanthi,Reddy, Ch. Srinivas
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p. 2126 - 2128
(2007/10/03)
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