scholarly journals A Solvent-Free Protocol for the Green Synthesis of 5-Arylidene-2,4-thiazolidinediones Using Ethylenediamine Diacetate as Catalyst

2012 ◽  
Vol 2012 ◽  
pp. 1-5 ◽  
Author(s):  
Yuliang Zhang ◽  
Zhongqiang Zhou

A simple and efficient synthesis of 5-arylidene-2,4-thiazolidinediones by the Knoevenagel condensation of aromatic aldehydes with 2,4-thiazolidinedione catalyzed by ethylenediamine diacetate under solvent-free conditions is described. The major advantages of this method are simple experimental and work-up procedures, solvent-free reaction conditions, small amount of catalyst, short reaction time, high yields, and utilization of an inexpensive and reusable catalyst.

2010 ◽  
Vol 8 (5) ◽  
pp. 1086-1089 ◽  
Author(s):  
Ramin Ghorbani-Vaghei ◽  
Seyedeh Malaekehpour

AbstractN,N,N,’N’-Tetrabromobenzene-1,3-disulfonamide [TBBDA] is found to be a reusable catalyst for efficient synthesis of various amidoalkyl naphthols from β-naphthol, aromatic aldehydes and urea in good to high yields under solvent-free conditions.


Author(s):  
Amir Khojastehnezhad

Silica supported molybdenum oxide (MoO<sub>3</sub>/SiO<sub>2</sub>) was found to be an efficient, eco-friendly and heterogeneous catalyst for the multicomponent reaction of aromatic aldehydes, dimedone and ammonium acetate or aromatic amines under solvent-free conditions to afford the corresponding 1,8-dioxodecahydroacridines  in high yields. The catalyst can be easily recovered and reused for several times without considerable loss of activity. Furthermore, the present method offers several advantages, such as an easy experimental and work-up procedures, short reaction times and good to excellent yields.


2019 ◽  
Vol 31 (6) ◽  
pp. 1357-1361 ◽  
Author(s):  
NARENDRA R. KAMBLE ◽  
VINOD T. KAMBLE

A combinatorial library of benzylpyrazolyl coumarin derivatives have been synthesized by a green one-pot four-component reaction between aryl hydrazine/hydrazine hydrate (1), ethyl acetoacetate (2), aromatic aldehydes (3) and 4-hydroxycoumarin (4) catalyzed by niobium pentachloride with silver salt under solvent-free conditions has been developed. Experimental simplicity, simple work-up procedure and solvent-free reaction condition at room temperature are important features of the present protocol.


2009 ◽  
Vol 87 (9) ◽  
pp. 1209-1212 ◽  
Author(s):  
Hongshe Wang ◽  
June Zeng

Chalcones are useful intermediates in organic synthesis and exhibit a large number of different biological activities. Chalcones have been synthesized in high yields by Claisen–Schmidt condensation of substituted acetophenones with various aromatic aldehydes in the presence of 10 mol% of iodine at room temperature by grinding under solvent-free conditions.


2013 ◽  
Vol 78 (6) ◽  
pp. 769-779 ◽  
Author(s):  
Ali Ghasemzadeh ◽  
Javad Safaei-Ghomi ◽  
Safura Zahedi

Magnetically separable Fe3O4 nanoparticles supply environmentally friendly procedure for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthene and 1,8-dioxo-octahydro-xanthene derivatives. These compounds were obtained in high yields and short reaction times by the reaction of dimedone and 2-naphthol with various aromatic aldehydes under solvent-free conditions. The catalyst coluld be easily recovered using an external magnet and reused for six cycles with almost consistent activity.


2020 ◽  
Vol 23 (4) ◽  
pp. 345-355
Author(s):  
Asef H. Najar ◽  
Zinatossadat Hossaini ◽  
Shahrzad Abdolmohammadi ◽  
Daryoush Zareyee

Aims & Objective: In this work ZnO-nanorod (ZnO-NR) as reusable catalyst promoted Strecker-type reaction of 2,4-dihydroxyacetophenone, isopropenylacetylene, trimethylsilyl cyanide (TMSCN), primary amines and isocyanides at ambient temperature under solvent-free conditions and produced α-amino nitriles benzofuran derivatives in high yields. These synthesized compounds may have antioxidant ability. Materials and Methods: ZnO-NRs in these reactions were prepared according to reported article. 2,4-dihydroxyacetophenone 1 (2 mmol) and isopropenylacetylene 2 (2 mmol) were mixed and stirred for 30 min in the presence of ZnO-NR (10 mol%) under solvent-free conditions at room temperature. After 30 min, primary amine 3 (2 mmol) was added to the mixture gently and the mixture was stirred for 15 min. After this time TMSCN 4 (2 mmol) was added to the mixture and stirred for 15 min. After completion of the reaction, as indicated by TLC, isocyanides 5 was added to mixture in the presence of catalyst. Results: In the first step of this research, the reaction of 2,4-dihydroxyacetophenone 1, isopropenylacetylene 2, methyl amine 3a, trimethylsilyle cyanide 4 and tert-butyl isocyanides 5a was used as a sample reaction to attain the best reaction conditions. The results showed this reaction performed with catalyst and did not have any product without catalyst after 12 h. Conclusion: In conclusion, we investigate multicomponent reaction of 2,4-dihydroxyacetophenone 1, isopropenylacetylene 2, primary amines 3, trimethylsilyl cyanide 4 and isocyanides along with ZnO-NRs as reusable catalyst at room temperature under solvent-free conditions which generates α-amino nitrile benzofuran derivatives in high yields. The advantages of our method are high atom economy, green reaction conditions, higher yield, shorter reaction times, and easy work-up, which are in good agreement with some principles of green chemistry. The compounds 8c exhibit excellent DPPH radical scavenging activity and FRAP compared to synthetic antioxidants BHT and TBHQ.


2018 ◽  
Vol 15 (7) ◽  
pp. 982-988 ◽  
Author(s):  
Fahimeh S. Hosseini ◽  
Mohammad Bayat

Aim and Objectives: Development of simple synthetic routes for widely used organic compounds from readily available reagents is one of the major tasks in organic chemistry. Therefore, new approaches for increasing the molecular diversity of simple starting materials, are needed. Herein, an efficient synthesis of imidazo[1,2-a]pyridine, pyrido[1,2-a]pyrimidine and pyrido[1,2-a][1,3]diazepine derivatives is described. Materials and Methods: A one-pot, multi-component reaction of nitro ketene aminal derived from the addition of various 1,n-diamines to 1,1-bis(methylthio)-2-nitroethene with cyanoacetamide and aromatic aldehydes is described. The reactions are completed within 2-5 h, in ethanol at reflux, in good to high yields (70-93%). The structures of products were deduced from their IR, mass, 1H NMR, and 13C NMR spectra. Results: Optimal reaction conditions for the synthesis of products were obtained, when ethanol was used as the solvent at reflux. This protocol involves Michael reaction, imine–enamine tautomerization, and cyclization sequences. Conclusion: This work represents an efficient synthesis of imidazo[1,2-a]pyridine, pyrido[1,2-a]pyrimidine and pyrido[1,2-a][1,3]diazepine derivatives via a one-pot, multi-component reaction. The advantages of this protocol are mild conditions, easy accessibility of reactants, absence of catalyst, high atom economy, simple work-up and purification process with no chromatographic technique.


2019 ◽  
Vol 16 (6) ◽  
pp. 939-947 ◽  
Author(s):  
Behzad Zeynizadeh ◽  
Soleiman Rahmani ◽  
Arezu Hallaj

Aim and Objective: Nowadays, bisdimedones and 1,8-dioxo-octahydroxanthenes are considered as biologically active materials. Due to this, the synthesis of the mentioned materials is the subject of more interest. Although most of the reported methods have their own merits, however, they generally require the use of expensive reagents, hazardous organic solvents, a tedious workup procedure and reduced recyclability of the applied catalyst system. Overcoming of the above mentioned drawbacks, therefore, encouraged us to investigate the capability of nanostructured NiFe2O4@Cu towards the synthesis of bisdimedones and 1,8- dioxo-octahydroxanthenes under green reaction conditions. Materials and Methods: Nanoparticles of NiFe2O4@Cu were prepared via a two-step procedure including the preparation of NiFe2O4 by solid-state grinding of Ni(OAc)2·4H2O and Fe(NO3)3·9H2O in the presence of NaOH followed by the immobilization of Cu(0) on the surface of NiFe2O4 nucleus via hydrazine hydrate reduction of Cu(NO3)2·3H2O. Results: After the synthesis of NiFe2O4@Cu, the catalytic activity of the Cu-nanocatalyst towards Knoevenagel reaction of aromatic aldehydes with dimedone under different reaction conditions was investigated. The examinations showed that using the molar equivalents of aromatic aldehydes (1 mmol) and dimedone (2 mmol) in the presence of 0.15 g NiFe2O4@Cu under solvent-free conditions chemoselectively afforded structurally different bisdimedone products at 60°C and 1,8-dioxo-octahydroxanthenes at 120°C. Conclusion: In this study, magnetically, nanoparticles of NiFe2O4@Cu were prepared and then characterized using different analyses. The catalytic activity of the prepared Cu-nanocatalyst was also studied towards solvent-free Knoevenagel condensation of aromatic aldehydes with dimedone. All the reactions were carried out within 15-240 min to afford bisdimedone and 1,8-dioxo-octahydroxanthene products in high yields.


2011 ◽  
Vol 8 (s1) ◽  
pp. S462-S466 ◽  
Author(s):  
Seied Ali Pourmousavi ◽  
Maryam Hasani

H2SO4-Silica efficiently catalyzes the three-component condensation reaction of aldehydes, 1,3-dicarbonyl compounds and urea/thiourea under solvent free conditions to afford the corresponding dihydropyrimidinones and thio-derivatives in high yields. Compared to the classical Biginelli reaction conditions, this new method consistently has the advantage of giving good yields and requiring short reaction times.


2019 ◽  
Vol 150 (12) ◽  
pp. 2021-2023 ◽  
Author(s):  
Ágnes Magyar ◽  
Zoltán Hell

Abstract A simple and efficient method for the synthesis of 2,2′-arylmethylenebis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) derivatives using 4 Å molecular sieves as catalyst is described. This approach offers several advantages such as high yields, mild reaction conditions, easily accessible, and reusable catalyst, and simple work-up procedure. Graphic abstract


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