Adipic Acid as a Biodegradable Solid Acid Catalyst for One-Pot, Three Component Synthesis of 1-Amidoalkyl-2-naphthols

2019 ◽  
Vol 7 (1) ◽  
pp. 34-43
Author(s):  
Hassan Darbandi ◽  
Hamzeh Kiyani
Keyword(s):  
Adipic Acid ◽  
Biological Activities ◽  
Condensation Reaction ◽  
Solid Acid Catalyst ◽  
Reaction Times ◽  
Acid Catalyst ◽  
Ultrasonic Waves ◽  
One Pot ◽  
Solvent Free Conditions ◽  
High Yields

Background: 1-Amidoalkyl-2-naphthols are an attractive group of organic compounds that can be converted to oxazine heterocycles and aminoalkyl naphthols. The derivatives of 1- amidoalkyl-2-naphthols have significant biological activities and act as drug candidates. Methods: 1-Amidoalkyl-2-naphthols were synthesized via the three-component condensation reaction of 2-naphthol, acetamide/benzamide and various aldehydes in the presence of 10 mol% of adipic acid as an organocatalyst under solvent-free conditions at 120°C. Results: A simple, efficient, and operative method for the synthesis of 1-amidoalkyl-2-naphtholes in the presence of adipic acid as the biodegradable catalyst is introduced. Easy operation, acceptable reaction times, eco-friendly, availability of starting materials, simple separation of products, and high yields of products are the significant results of this method. Conclusion: In this study, 1-amidoalkyl-2-naphthols were synthesized using commercially available reactants in excellent yields and relatively shorter times. In this process, microwave or ultrasonic waves were not used to provide energy for the reaction.

scholarly journals Citric acid as a green and naturally biodegradable catalyst promoted convenient synthesis of polysubstituted dihydro-2-oxypyrrole derivatives via four-condensation reaction of dialkylacetylenedicarboxylate, formaldehyde and amines

2019 ◽  
Vol 9 (4) ◽  
pp. 4096-4100
Keyword(s):  
Citric Acid ◽  
Low Cost ◽  
Condensation Reaction ◽  
Solid Acid Catalyst ◽  
Reaction Times ◽  
Acid Catalyst ◽  
One Pot ◽  
Convenient Synthesis ◽  
High Yields ◽  
Work Up

Citric acid is found to be a green and naturally biodegradable catalyst for one-pot, four-condensation of dialkylacetylenedicarboxylate, formaldehyde and amines (aromatic and aliphatic) to afford the corresponding polysubstituted dihydro-2-oxypyrrole derivatives under ambient temperature. The remarkable features of this one-pot procedure are green and low-cost catalyst, high yields, short reaction times, simplicity of operation and work-up procedures, the availability and easy to handle of this solid acid catalyst, avoidance of hazardous or toxic catalyst and mild reaction conditions.

scholarly journals One-Pot Synthesis ofβ-Acetamido Ketones Using Boric Acid at Room Temperature

2012 ◽  
Vol 2012 ◽  
pp. 1-4 ◽  
Author(s):  
Zahed Karimi-Jaberi ◽  
Korosh Mohammadi
Keyword(s):  
Boric Acid ◽  
Room Temperature ◽  
Simple Procedure ◽  
Condensation Reaction ◽  
Solid Acid Catalyst ◽  
Reaction Times ◽  
Acid Catalyst ◽  
One Pot ◽  
Green Catalyst ◽  
One Pot Condensation

β-acetamido ketones were synthesized in excellent yields through one-pot condensation reaction of aldehydes, acetophenones, acetyl chloride, and acetonitrile in the presence of boric acid as a solid heterogeneous catalyst at room temperature. It is the first successful report of boric acid that has been used as solid acid catalyst for the preparation ofβ-acetamido ketones. The remarkable advantages offered by this method are green catalyst, mild reaction conditions, simple procedure, short reaction times, and good-to-excellent yields of products.

A new procedure for the preparation of 3,4-dihydropyrimidin-2(1H)-one and octahydroquinazolinone derivatives catalyzed by SCMNPs@CA-EA-SO3H under solvent-free conditions

2021 ◽  
Vol 19 ◽  
Author(s):  
Asieh Yahyazadeh ◽  
Motahare Nafei-Kohi ◽  
Esmayeel Abbaspour-Gilandeh ◽  
Mehraneh Aghaei-Hashjin
Keyword(s):  
Solid Acid Catalyst ◽  
Reaction Times ◽  
Acid Catalyst ◽  
Solvent Free ◽  
One Pot ◽  
Reaction Solution ◽  
Solvent Free Conditions ◽  
The One ◽  
Heterogeneous Solid ◽  
Octahydroquinazolinone Derivatives

Abstract: Catalyzed with SCMNPs@CA-EA-SO3H, as a green and heterogeneous solid acid catalyst, 3,4-dihydropyrimidin-2(1H)-one and octahydroquinazolinone derivatives were obtained in high-to-excellent yields and in short reaction times via the one-pot multi-component condensation of ethyl acetoacetate or dimedone, urea, and aldehyde compounds under solvent-free conditions. More importantly, the green catalytic system could be easily collected from the reaction solution utilizing an external magnet and reused for five runs with a negligible decrease in yields and reaction rate.

An efficient, Green Synthesis of benzo[a]furo[2, 3-c]phenazine derivatives via Microwave-Assisted and TiO2-SO3H as Cost-effective and Recyclable Catalyst under solvent-free conditions

2020 ◽  
Vol 17 ◽  
Author(s):  
Milad Taheri ◽  
Razieh Mohebat ◽  
Mohammad Hossein Moslemin
Keyword(s):  
Microwave Irradiation ◽  
Solid Acid Catalyst ◽  
Internal Standard ◽  
Acid Catalyst ◽  
Cost Effective ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
High Yields ◽  
Recyclable Heterogeneous Catalyst

Background: A rapid, efficient, and environmentally benign procedure for the synthesis of novel furo [2,3- c]phenazine derivatives has been developed via reactions of 2-hydroxynaphthalene-1,4-dione, arylglyoxals, and indole in the presence of TiO2-SO3H-catalyst (TSAC) as a recyclable heterogeneous catalyst under solvent-free conditions using microwave irradiation. Introduction: This study describes a successful approach for the synthesis of 2-(4-bromophenyl)-1-(1H-indol-3-yl) benzo[a]furo[2,3-c] phenazine via TiO2-SO3H-catalyst using microwave irradiation. Objectives: In this paper, we wish to report an efficient and convenient method for the synthesis of phenazine derivatives from benzo[a]phenazin-5-ol, arylglyoxal derivatives, and Indoles in the presence of TiO2-SO3H-catalyst under microwave irradiation. Materials and Methods: All reagents and solvent were purchased from Merck and Aldrich and used without further purification. 1H NMR spectra (DMSO) were recorded on Gemini-500 MHz spectrophotometer with TMS as internal standard. Results and Discussions: To investigate the reaction conditions for the synthesis of 2-(4-bromophenyl)-1-(1H-indol-3-yl) benzo[a]furo [2, 3-c] phenazine derivatives, we performed a reaction between 2-hydroxynaphthalene-1,4-dione (1 mmol) and aromatic 1,2-diamines (1 mmol) as a model. Conclusion: We demonstrated a green and straightforward procedure for the efficient synthesis of novel benzo[a]furo[2, 3- c] phenazine derivatives in high yields via a one-pot, four-component domino protocol by using TiO2-SO3H as a mild, effective, non-toxic, and inexpensive solid acid catalyst without the addition of an organic co-solvent.

scholarly journals Phosphosulfonic acid, an efficient solid acid catalyst for the one-pot preparation of 14-aryl-14H-dibenzo[a,j]xanthenes and 1,8-dioxo-octahydro-xanthenes under solvent-free conditions

2013 ◽  
Vol 78 (9) ◽  
pp. 1291-1299 ◽  
Author(s):  
Reza Kiasat ◽  
Arash Mouradzadegun ◽  
Jafar Saghanezhad
Keyword(s):  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
One Pot ◽  
Aryl Aldehydes ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields

An expeditious procedure for the synthesis of 14- aryl-14H-dibenzo[a,j]xanthenes and 1,8-dioxo-octahydro-xanthenes through one-pot pseudo three component condensation of ?-naphthol or dimedone with various aryl aldehydes is described. This greener protocol is catalyzed by phosphosulfonic acid, and proceeds efficiently in the absence of any organic solvent under optimized, mild, green and environmentally benign reaction conditions in high yields within 20-55 minutes.

Study of the Catalytic Activity of Zr(HPO4)2 in the Synthesis of Hexahydroquinoline Derivatives under Solvent-free Conditions

2013 ◽  
Vol 68 (2) ◽  
pp. 195-200 ◽  
Author(s):  
Shahrzad Abdolmohammadi
Keyword(s):  
Catalytic Activity ◽  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields

2-Amino-7,7-dimethyl-5-oxo-1,4-diaryl-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile derivatives were synthesized by the one-pot four-component reaction of aromatic aldehydes, malononitrile, dimedone and arylamines in the presence of Zr(HPO4)2·H2O (α-ZrP) as an effective and recyclable solid acid catalyst, in high yields.

scholarly journals H2SO4-Silica Catalyzed One-Pot and Efficient Synthesis of Dihydropyrimidinones Under Solvent-Free Conditions

2011 ◽  
Vol 8 (s1) ◽  
pp. S462-S466 ◽  
Author(s):  
Seied Ali Pourmousavi ◽  
Maryam Hasani
Keyword(s):  
Condensation Reaction ◽  
Biginelli Reaction ◽  
Reaction Times ◽  
Solvent Free ◽  
New Method ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Solvent Free Conditions ◽  
High Yields

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.

A highly efficient and green approach for the synthesis of pyrimido[4,5-b]quinolines using N,N-diethyl-N-sulfoethanaminium chloride

2021 ◽  
Vol 76 (2) ◽  
pp. 85-90
Author(s):  
Abdolkarim Zare ◽  
Manije Dianat
Keyword(s):  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Catalyst Amount ◽  
Green Protocol ◽  
Highly Efficient ◽  
Green Approach ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields

Abstract A highly efficient and green protocol for the synthesis of pyrimido[4,5-b]quinolines has been described. The one-pot multicomponent reaction of dimedone with arylaldehydes and 6-amino-1,3-dimethyluracil in the presence of N,N-diethyl-N-sulfoethanaminium chloride ([Et3N–SO3H][Cl]) as an ionic liquid (IL) catalyst under solvent-free conditions afforded the mentioned compounds in high yields and short reaction times. Our protocol is superior to many of the reported protocols in terms of two or more of these factors: the reaction times, yields, conditions (solvent-free versus usage of organic solvents), temperature and catalyst amount.

Rapid and Green One-Pot Synthesis of Novel 2-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-diones

2021 ◽  
Vol 18 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Zahra Ghahremany ◽  
Madieh Sadeghpour
Keyword(s):  
Aromatic Amines ◽  
Low Cost ◽  
Guanidine Hydrochloride ◽  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields ◽  
Work Up

: A green and efficient protocol was developed for the one-pot three-component synthesis of novel 2-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-dione derivatives by the reaction of 4-hydroxycoumarin, ninhydrin and aromatic amines in the presence of guanidine hydrochloride as an organocatalyst under solvent-free conditions. The present approach offers several advantages such as low cost, simple work-up, short reaction times, chromatography-free purification, high yields and greener conditions.

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