Ultrasound-assisted aqua-mediated synthesis of multi-substituted tetrahydropyridine-3-carboxylates using N-carboxymethyl-3-pyridinium hydrogensulfate ([N-CH2CO2H-3-pic]+HSO4−) as a new efficient ionic liquid catalyst

2021 ◽  
Vol 3 (6) ◽  
Author(s):  
Kobra Nikoofar ◽  
Fatemeh Shahriyari
Keyword(s):  
Ionic Liquid ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
H Nmr ◽  
Sonic Waves ◽  
Ft Ir ◽  
High Yields ◽  
Work Up ◽  
C Nmr

AbstractA simple, straightforward, and ultrasound-promoted method for the preparation of some highly functionalized tetrahydropyridines reported via pseudo five-component reaction of (hetero)aromatic aldehydes, different anilines, and alkyl acetoacetates in the presence of [N-CH2CO2H-3-pic]+HSO4−, as a novel ionic liquid, in green aqueous medium. The IL was synthesized utilizing simple and easily-handled substrates and characterized by FT-IR, 1H NMR, 13C NMR, GC-MASS, FESEM, EDX, and TGA/DTG techniques. The procedure contains some highlighted aspects which are: (a) performing the MCR in the presence of aqua and sonic waves, as two main important and environmentally benign indexes in green and economic chemistry, (b) high yields of products within short reaction times, (c) convenient work-up procedure, (d) preparing the new IL via simple substrates and procedure.

Facile synthesis of 3-arylidene-1,3-dihydroindol-2-ones catalysed by a Brønsted acidic ionic liquid

2008 ◽  
Vol 2008 (11) ◽  
pp. 642-643 ◽  
Author(s):  
Yi Hu ◽  
Hui Kang ◽  
Bi-Wen Zeng ◽  
Ping Wei ◽  
He Huang
Keyword(s):  
Ionic Liquid ◽  
High Purity ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Facile Synthesis ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
High Yields ◽  
Work Up

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.

One Pot Three Component Synthesis of 9-arylpolyhydroacridine Derivatives in an Ionic Liquid Medium

2005 ◽  
Vol 2005 (9) ◽  
pp. 600-602 ◽  
Author(s):  
Yu-Ling Li ◽  
Mei-Mei Zhang ◽  
Xiang-Shan Wang ◽  
Da-Qing Shi ◽  
Shu-Jiang Tu ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Ammonium Acetate ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
One Pot ◽  
High Yields ◽  
Work Up ◽  
Ionic Liquid Medium

In this paper the preparation of 3,3,6,6-tetramethyl-9-aryl-1,2,3,4,5,6,7,8,9,10- decahydroacridin-1,8-dione derivatives from aromatic aldehydes, 5,5-dimethyl-1,3- cyclohexanedione and ammonium acetate in ionic liquids [bmim+][BF4-] is described. This new method has the advantages of easier work-up, milder reaction conditions, high yields and an environmentally benign procedure compared with other methods.

An efficient synthesis of imidazo[2,1-b][1,3,4]thiadiazol-7-ium hydroxides by a one-pot, three-component reaction in water

2018 ◽  
Vol 24 (6) ◽  
pp. 297-302 ◽  
Author(s):  
Jabbar Khalafy ◽  
Nasser Etivand ◽  
Neda Khalillou
Keyword(s):  
Reaction Times ◽  
Sulfamic Acid ◽  
One Pot ◽  
Green Protocol ◽  
H Nmr ◽  
Three Component Reaction ◽  
Ft Ir ◽  
High Yields ◽  
Reaction In Water ◽  
C Nmr

Abstract An improved synthesis of 2-ethyl-5-(2-hydroxy-4-oxoquinolin-3(4H)-ylidene)-6-aryl-5,6-dihydroimidazo[2,1-b][1,3,4]thiadiazol-7-ium hydroxide derivatives 4a–k via the reaction of aryl glyoxal monohydrates 1a–k, quinoline-2,4-diol 2 and 2-amino-[1,3,4]thiadiazole (3) in the presence of Et3N/sulfamic acid in H2O is described. This green protocol is characterized by the use of the readily available catalyst and reactants, short reaction times, operational simplicity and high yields of products. The structures of all compounds were characterized by 1H NMR, 13C NMR and Fourier-transform infrared (FT-IR) spectral data and microanalyses.

Design, preparation and characterization of a new ionic liquid, 1,3-disulfonic acid benzimidazolium chloride, as an efficient and recyclable catalyst for the synthesis of tetrahydropyridine under solvent-free conditions

RSC Advances ◽  
2015 ◽  
Vol 5 (83) ◽  
pp. 67405-67411 ◽  
Author(s):  
Mohsen Abbasi
Keyword(s):  
Ionic Liquid ◽  
Mass Spectra ◽  
Recyclable Catalyst ◽  
Solvent Free ◽  
Disulfonic Acid ◽  
H Nmr ◽  
Solvent Free Conditions ◽  
Ft Ir ◽  
C Nmr

In the present work, 1,3-disulfonic acid benzimidazolium chloride as a new ionic liquid, is synthesized, and characterized by studying its FT-IR, 1H NMR, 13C NMR as well as mass spectra.

CeCl3·7H2O as mild and efficient catalyst for the one-pot multicomponent synthesis of 8-aryl-7,8-dihydro[1,3]dioxolo[4,5-g]chromen-6-ones

2011 ◽  
Vol 76 (4) ◽  
pp. 235-241 ◽  
Author(s):  
Li-Qiang Wu ◽  
Wei-Lin Li ◽  
Fu-Lin Yan
Keyword(s):  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Three Component Reaction ◽  
The One ◽  
High Yields ◽  
Work Up

A series of new 8-aryl-7,8-dihydro[1,3]dioxolo[4,5-g]chromen-6-ones were synthesized via a three-component reaction of 3,4-methylenedioxyphenol, aromatic aldehydes and Meldrum’s acid in the presence of CeCl3·7H2O under solvent-free conditions. The method provided several advantages such as easy work-up, high yields and environmentally benign procedure.

scholarly journals Synthesis of New Imidazolidine and Tetrahydropyrimidine Derivatives

2014 ◽  
Vol 2014 ◽  
pp. 1-4 ◽  
Author(s):  
Hamid Beyzaei ◽  
Reza Aryan ◽  
Zahra Keshtegar
Keyword(s):  
Ring Opening ◽  
Reaction Times ◽  
Reaction Conditions ◽  
Ir Spectrometry ◽  
H Nmr ◽  
Chemical Structures ◽  
Thioamide Group ◽  
Solvent Free Conditions ◽  
Ft Ir ◽  
C Nmr

Synthesis of new imidazolidine and tetrahydropyrimidine derivatives 3a, b and 4a–c as cyclic 1,3-diamines under two reaction conditions (A and B) is described. Under reaction conditions-A, a suspension of (E)-2-cyano-2-(oxazolidin-2-ylidene)ethanethioamide 1 (1 eq.) and diaminoalkanes 2a–e (2 eq.) in absolute ethanol is heated under reflux for 16–22 h to afford 3a, b and 4a–c. Alternatively, under reaction conditions-B, a solution of thioamide 1 (1 eq.) in diaminoalkanes 2a–e (3 eq.) is stirred under solvent-free conditions at room temperature for 3 days to give desired products. Reaction conditions-A for having higher yields, shorter reaction times, and required less diamines is more effective than reaction conditions-B. Oxazolidine ring opening is observed by reacting compound 1 with all of the diamines 2a–e, but the thioamide group only reacts with nonbulky diamines 2a, b. The chemical structures of novel compounds were confirmed by 1H NMR, 13C NMR, elemental analysis, and FT-IR spectrometry.

H3PW12O40 — A selective, environmentally benign, and reusable catalyst for the preparation of methoxymethyl and ethoxymethyl ethers and their deprotections under mild conditions

2008 ◽  
Vol 86 (8) ◽  
pp. 831-840 ◽  
Author(s):  
Iraj Mohammadpoor-Baltork ◽  
Majid Moghadam ◽  
Shahram Tangestaninejad ◽  
Valiollah Mirkhani ◽  
Arsalan Mirjafari
Keyword(s):  
Reaction Times ◽  
Environmentally Benign ◽  
Reusable Catalyst ◽  
Secondary Alcohols ◽  
Selective Protection ◽  
Trimethylsilyl Ethers ◽  
Solvent Free Conditions ◽  
Benzyl Ethers ◽  
High Yields ◽  
Work Up

Different types of primary and secondary alcohols were efficiently transformed to their corresponding methoxymethyl (MOM) and ethoxymethyl (EOM) ethers in the presence of catalytic amounts of H3PW12O40 at room temperature under solvent-free conditions. Selective protection of primary and secondary alcohols in the presence of phenols and tertiary alcohols was achieved by this method. Deprotection of these ethers to their parent alcohols was also performed using this catalyst in ethanol under reflux conditions. We have also found that primary and secondary MOM- and EOM-ethers are selectively deprotected in the presence of phenolic and tertiary ones, methyl and benzyl ethers, esters, and trimethylsilyl ethers by this catalyst. The notable advantages of this protocol are high yields, short reaction times, easy work-up, non-toxicity, easy availability and handling, eco-friendly, and reusability of the catalyst.Key words: methoxymethylation, ethoxymethylation, protection, deprotection, heteropoly acid.

scholarly journals Synthesis and Spectroscopic Characterization of Some New Biological Active Azo–Pyrazoline Derivatives

2012 ◽  
Vol 9 (3) ◽  
pp. 1613-1622 ◽  
Author(s):  
Farouq E. Hawaiz ◽  
Mohammad K. Samad
Keyword(s):  
Addition Reaction ◽  
Coupling Reaction ◽  
Spectroscopic Characterization ◽  
Hydroxyl Group ◽  
Significant Activity ◽  
H Nmr ◽  
Ft Ir ◽  
High Yields ◽  
C Nmr

A number of 3-[4-(benzyloxy)-3-(2-Chlorophenylazo)-phenyl]-5-(substituted-phenyl)-1-substituted-2-pyrazolines( 4a-j) and (5a-j) have been synthesized by diazotization of 2-chloroaniline and its coupling reaction with 4-hydroxy acetophenone, followed by benzyloxation of the hydroxyl group to give the substrate [4-benzyloxy-3-(2-chlorophenylazo)-acetophenone (1)].The prepared starting material (1) has been reacted with different substituted benzaldehydes to give a new series of chalcone derivatives 1-[(4-benzyloxy)-3-(2-chloro-phenylazo)-phenyl]-3-(substituted phenyl)-2-propen-1-one (3a-j), in high yields and in a few minutes, and the later compounds were treated with hydrazine hydrate according to Michael addition reaction to afford a new biolological active target compounds (4a-j) and (5a-j). Furthermore, The structures of the newly synthesized compounds were confirmed by FT-IR,13C-NMR,13C-DEPT &1H-NMR spectral data. The chalcone and pyrazoline derivatives were evaluated for their anti bacterial activity againstEscherichia colias gram negative andStaphylococcus aureusas gram positive, the results showed significant activity against both types of bacteria.

scholarly journals Leucine: green and efficient catalyst for the synthesis of 4H-chromenes

2017 ◽  
Vol 10 (9) ◽  
pp. 3197-3202 ◽  
Author(s):  
Davood Azarifar ◽  
Younes Abbasi ◽  
Omolbanin Badalkhani
Keyword(s):  
Amino Acid ◽  
Condensation Reaction ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
One Pot ◽  
Efficient Catalyst ◽  
Naturally Occurring ◽  
The One ◽  
High Yields ◽  
Work Up

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. 

One-Pot Solvent-and Catalyst-Free Synthesis of Some New Heteroarylaminonaphthoquinones from Lawsone

2021 ◽  
Vol 18 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Nilufar Rahmani ◽  
Mahdieh Sadeghpour ◽  
Amir Mohamadi
Keyword(s):  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Heterocyclic Amines ◽  
Environmentally Benign ◽  
One Pot ◽  
Simple Operation ◽  
Catalyst Free ◽  
Three Component Reaction ◽  
Methyl Naphthalene ◽  
Work Up

: A clean and efficient one-pot protocol for the synthesis of a series of new 2-hydroxy-3-((3-aryl)(heteroarylamino)methyl)naphthalene-1,4-dione derivatives has been developed by the three-component reaction of 2-hydroxynaphthalene-1,4-dione, aromatic aldehydes and heterocyclic amines at 90 oC under solvent and catalyst-free conditions. The procedure avoids the use of toxic solvents, tedious work-up, catalyst and purification of the products by chromatographic methods. Simple operation, short reaction times, generating the desired compounds in high to excellent yields and an environmentally benign method are advantages of this protocol.

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