scholarly journals Efficient Synthesis of 12-Aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-ones using Ionic Liquid Pyrazinium Di(hydrogen sulfate) {Py(HSO4)2} as a Novel, Green and Homogeneous Catalyst

2017 ◽  
Vol 56 (4) ◽  
Author(s):  
Abdolkarim Zare ◽  
Roghayyeh Khanivar ◽  
Marzieh Hatami ◽  
Mohammad Mokhlesi ◽  
Mohammad Ali Zolfigol ◽  
...  

An efficient and simple solvent-free procedure for the synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[<em>a</em>]-xanthen-11-one derivatives <em>via</em> the one-pot multi-component condensation of dimedone with aromatic aldehydes and β-naphthol in the presence of protic acidic ionic liquid pyrazinium di(hydrogen sulfate) {Py(HSO<sub>4</sub>)<sub>2</sub>} as a green and homogeneous catalyst is described. All reactions proceed efficiently, and the title compounds are produced in high yields and in short reaction times.

RSC Advances ◽  
2015 ◽  
Vol 5 (30) ◽  
pp. 23586-23590 ◽  
Author(s):  
Kamal Mohammadi ◽  
Farhad Shirini ◽  
Asieh Yahyazadeh

1,3-Disulfonic acid imidazolium hydrogen sulfate (DSIMHS) has been used for the simple and efficient synthesis of pyrimido[4,5-b]quinoline derivatives. The procedure gave the products in excellent yields in very short reaction times.


2020 ◽  
Vol 23 (2) ◽  
pp. 157-167
Author(s):  
Zainab Ehsani-Nasab ◽  
Ali Ezabadi

Objective: A facile and efficient method for synthesis of 3, 4-dihydropyrimidin-2(1H)-ones via Biginelli reaction catalyzed by a novel dicationic Brönsted acidic ionic liquid, [(EtNH2)2SO][HSO4]2, has been successfully developed. Material and Method:: 3, 4-Dihydropyrimidin-2(1H)-ones were synthesized through one-pot condensation of aromatic aldehydes, ethyl acetoacetate, and urea under solvent-free conditions using [(EtNH2)2SO][HSO4]2 as a novel catalyst. The progress of the reaction was monitored by thin-layer chromatography (ethyl acetate / n-hexane = 1 / 5). The products have been characterized by IR, 1H NMR, 13C NMR, and also by their melting points. Results: In this research, a library of dihydropyrimidinone derivatives was synthesized via Biginelli reaction under solvent-free conditions at 120oC using [(EtNH2)2SO][HSO4]2 as a catalyst. Various aromatic aldehydes, as well as heteroaromatic aldehydes, were employed, affording good to high yields of the corresponding products and illustrating the substrate generality of the present method. In addition, the prepared dicationic Brönsted acidic ionic liquid can be easily recovered and reused. Conclusion: 1, 1’-Sulfinyldiethylammonium bis (hydrogen sulfate), as a novel dicationic ionic liquid, can act as a highly efficient catalyst for the synthesis of 3, 4-dihydropyrimidin-2(1H)-ones under solvent-free conditions.


2016 ◽  
Vol 69 (9) ◽  
pp. 1049 ◽  
Author(s):  
Sudesh Kumari ◽  
M. Rajeswari ◽  
Jitender M. Khurana

A multicomponent reaction capable of affording a wide range of novel 7,11-dihydro-6H-chromeno[3,4-e]isoxazolo[5,4-b]pyridin-6-one derivatives via one-pot three-component condensation of 4-hydroxycoumarin, aromatic aldehydes, and 5-amino-3-methylisoxazole in ionic liquid 1-butyl-3-methylimidazolium hydrogen sulfate ([C4mim][HSO4]) is reported. Structures have been confirmed by spectral and X-ray studies. Crystal packing of 4b has also been reported. Green solvent, short reaction time, easy workup, and high yields are the salient features of the present protocol.


2008 ◽  
Vol 5 (4) ◽  
pp. 688-695 ◽  
Author(s):  
Taoues Boumoud ◽  
Boudjemaa Boumoud ◽  
Salah Rhouati ◽  
Ali Belfaitah ◽  
Abdelmadjid Debache ◽  
...  

The Biginelli one-pot three-component cyclocondensation was applied in this work to prepare 3,4-dihydropyrimidinone and its analogues using the first derivative of lead, Pb(NO3)2, as a recycling catalyst, from a diversity of aromatic aldehydes, β-ketoesters and urea. The reaction was carried out in refluxing acetonitrile and afforded the target molecules in good to excellent yields. The method offers several advantages including high yields of the products, short reaction times and easy experimental workup procedure


2017 ◽  
Vol 10 (9) ◽  
pp. 3197-3202 ◽  
Author(s):  
Davood Azarifar ◽  
Younes Abbasi ◽  
Omolbanin Badalkhani

Leucine, a naturally occurring α-amino acid, has been found as an effective catalyst to effect the one-pot three-component condensation reaction between aromatic aldehydes, malononitrile and 5,5-dimethyl-1,3-cyclohexanedione (dimedone). Various 2-amino-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile derivatives are conveniently prepared by these reactions in excellent yields. High yields, short reaction times, simple work-up, use of green and naturally occurring catalyst and solvent are the main merits of the present protocol. 


2008 ◽  
Vol 2008 (11) ◽  
pp. 642-643 ◽  
Author(s):  
Yi Hu ◽  
Hui Kang ◽  
Bi-Wen Zeng ◽  
Ping Wei ◽  
He Huang

A series of 3-arylidene-1,3-dihydroindol-2-one derivatives were conveniently synthesised by the condensation of aromatic aldehydes with 1,3-dihydroindol-2-one using a Brønsted acidic ionic liquid as a dual solvent-catalyst. This method has the advantages of short reaction times, simple work-up, high yields with high purity, being environmentally benign and the ionic liquid can be reused.


2017 ◽  
Vol 41 (3) ◽  
pp. 136-138 ◽  
Author(s):  
Sabereh Bougan ◽  
Alireza Hassanabadi

A green and efficient synthesis of the title compounds has been achieved in a one-pot, three-component reaction of 4-hydroxycoumarin and aromatic aldehydes with methyl carbamate catalysed by p-toluenesulfonic acid in aqueous media to afford 4-aryl-3,4-dihydrochromeno[3,4-e][1,3]oxazine-2,5-diones in excellent yields. The salient features of this protocol are: short reaction times, high yields and absence of any hazardous organic solvent. Consequently, this procedure could be classified as green chemistry.


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.


2014 ◽  
Vol 68 (8) ◽  
Author(s):  
Hamzeh Kiyani ◽  
Fatemeh Ghorbani

Abstract2-Amino-4-aryl-4H-benzo[h]chromenes and 3-amino-1-aryl-1H-benzo[f]chromenes were prepared by treating cyano-methylene compounds (malononitrile or ethyl cyanoacetate), substituted aromatic aldehydes, and naphtholic compounds in the presence of potassium phthalimide as a green, mild, efficient, and commercially available organocatalyst in aqueous media. The procedure was readily conducted and affords remarkable advantages such as safety, short reaction times, environmentally benign milder reaction conditions, no organic solvent required, and high yields.


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