scholarly journals Marine solids/NaNO3: As Natural and Efficient Catalysts for Aldol condensation

2018 ◽  
Vol 9 (1) ◽  
Author(s):  
Azar Mostoufi ◽  
Mohammad Reza Shushizadeh ◽  
Aedeh Sayahi ◽  
Seyed Mohammad Bagher Nabavi ◽  
Bahar Mohandespour
Keyword(s):  
Carbonyl Compounds ◽  
Aldol Condensation ◽  
Melting Points ◽  
Efficient Catalyst ◽  
Sem Image ◽  
H Nmr ◽  
Aldehydes And Ketones ◽  
Infrared Spectrometer ◽  
High Yields ◽  
Carbonyl Products

A new and efficient method have been developed for the synthesis of α,β-unsaturated carbonyl compounds from various aldehydes and ketones, using marine calcinated coral/NaNO3 and cuttlebone/NaNO3, as natural and efficient catalysts for cross aldol condensation. The aim of present study was to study the marine solids/NaNO3: as natural and efficient catalyst for Aldol condensation. The materials were purchased from Merck and Aldrich Companies. The IR spectra were recorded on a Perkin-Elmer RXI infrared spectrometer. H NMR spectra were recorded on a 400 MHz Brucker FT-NMR spectrometer. The SEM image was recorded on 1455 VP LEO-Germany. TLC accomplished the purity of substrates and reactions monitored on silica gel (Merck, Germany) Polygram SIGL/UV254 plates. The melting points are uncorrected. Results showed that, the marine solid are efficient catalysts for aldol condensation, but cuttlebone/NaNO3 catalyze this reaction in shorter time (1 hr) than calcinated coral/NaNO3 (6 hr). However, these marine solids have several advantages such as small amount of the catalyst, good absorbent natural solid, easy to handle, and products in good-to-high yields. In conclusion we found marine catalysts, Calcinated Cuttlebone/NaNO3 or Coral/NaNO3 to be an effective catalyst for aldol condensation from ketones having α-hydrogens and aldehydes in 50 % ethanol at reflux conditions. The α,β-unsaturated carbonyl products were obtained in good to high yields. This method offered marked improvement compared to previously reported ones.

scholarly journals Copper(I) Chloride/Kieselguhr: A Versatile Catalyst for Oxidation of Alkyl Halides and Alkyl Tosylates to the Carbonyl Compounds

1999 ◽  
Vol 23 (7) ◽  
pp. 434-435
Author(s):  
Mohammed M. Hashemi ◽  
Yousef Ahmadi Beni
Keyword(s):  
Carbonyl Compounds ◽  
Alkyl Halides ◽  
Aldehydes And Ketones ◽  
High Yields

Copper(I) Chloride adsorbed on Kieselguhr in the presence of oxygen catalyses oxidation of alkyl halides and alkyl tosylates to the aldehydes and ketones in high yields.

Chemoselective thioacetalization with odorless 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid as a 1,3-propanedithiol equivalent

2005 ◽  
Vol 83 (10) ◽  
pp. 1741-1745 ◽  
Author(s):  
Haifeng Yu ◽  
Dewen Dong ◽  
Yan Ouyang ◽  
Qun Liu
Keyword(s):  
Key Words ◽  
Carbonyl Compounds ◽  
Acetyl Chloride ◽  
Oxobutanoic Acid ◽  
Aldehydes And Ketones ◽  
Ketene Dithioacetal ◽  
High Yields

Odorless 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid (1c) was prepared and investigated in the thioacetalization of carbonyl compounds as a 1,3-propanedithiol equivalent. The results showed that the thioacetalization of various carbonyl compounds 2 with 1c proceeded smoothly and afforded the corresponding dithioacetals 3 in high yields (up to 99%) in the presence of acetyl chloride at room or reflux temperatures. Moreover, the thioacetalization exhibited high chemoselectivity between aldehydes and ketones. Key words: chemoselectivity, 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid, α-oxo ketene dithioacetal, 1,3-propanedithiol equivalent, thioacetalization.

Synthesis of Zingerone Using NiCl2•6H2O-NaBH4 as a Selective Hydrogenation Reaction Agent

2019 ◽  
Vol 948 ◽  
pp. 127-132
Author(s):  
Murdiah ◽  
Deni Pranowo ◽  
Tri Joko Raharjo
Keyword(s):  
Mild Condition ◽  
Selective Hydrogenation ◽  
Aldol Condensation ◽  
Condensation Reaction ◽  
Hydrogenation Reaction ◽  
Second Step ◽  
H Nmr ◽  
Ft Ir ◽  
High Yields ◽  
C Nmr

Synthesis of zingerone (4-(4-hydroxy-3-methoxyphenyl)-2-butanone) has been done. The first step was to synthesize the compound (4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-on) through a cross aldol condensation reaction between vanilin:acetone mol ratio of 1:5:5, for 5 hours in high yields (97%). The second step was the selective hydrogenation of (4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-on) with NiCl2•6H2O-NaBH4 catalyst in mild condition. Based on the FT-IR, 13C-NMR and 1H-NMR and GC-MS analyses, the synthesis of zingerone has been successfully synthesized by selective hydrogenation reaction with 80% yield.

A solvent-free protocol for facile condensation of indoles with carbonyl compounds using silica chloride as a new, highly efficient, and mild catalyst

2007 ◽  
Vol 85 (6) ◽  
pp. 416-420 ◽  
Author(s):  
Alireza Hasaninejad ◽  
Abdolkarim Zare ◽  
Hashem Sharghi ◽  
Mohsen Shekouhy ◽  
Reza Khalifeh ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Electrophilic Substitution ◽  
Room Temperature ◽  
Low Cost ◽  
Reaction Times ◽  
Catalytic Amount ◽  
Solvent Free ◽  
Substitution Reactions ◽  
Aldehydes And Ketones ◽  
High Yields

A simple and efficient solvent-free procedure for the preparation of bis(indolyl)methanes via electrophilic substitution reactions of indoles with aldehydes and ketones is described. The reactions took place in the presence of a catalytic amount of silica chloride at room temperature. The advantages of this method are high yields, short reaction times, low cost, and compliance with green-chemistry protocols.Key words: silica chloride, indole, carbonyl compound, solvent-free, bis(indolyl)methane.

Main group metal–ligand cooperation of N-heterocyclic germylene: an efficient catalyst for hydroboration of carbonyl compounds

2016 ◽  
Vol 52 (95) ◽  
pp. 13799-13802 ◽  
Author(s):  
Yile Wu ◽  
Changkai Shan ◽  
Ying Sun ◽  
Peng Chen ◽  
Jianxi Ying ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Main Group ◽  
Efficient Catalyst ◽  
Mild Conditions ◽  
Group Metal ◽  
Main Group Metal ◽  
Aldehydes And Ketones ◽  
Substrate Tolerance ◽  
Metal Ligand ◽  
Operational Simplicity

N-heterocyclic ylide-like germylene effectively promotes the hydroboration of aldehydes and ketones under mild conditions with broad substrate tolerance, operational simplicity of the procedure and excellent yields.

scholarly journals Synthesis and Nitration of 7-Hydroxy-4-Methyl Coumarin via Pechmann Condensation Using Eco-Friendly Medias

2016 ◽  
Vol 69 ◽  
pp. 66-73 ◽  
Author(s):  
Fadia Al Haj Hussien ◽  
Mohammad Keshe ◽  
Khaled Alzobar ◽  
Joumaa Merza ◽  
Ayman Karam
Keyword(s):  
Biological Activity ◽  
Coumarin Derivatives ◽  
Melting Points ◽  
Efficient Catalyst ◽  
Amberlyst 15 ◽  
H Nmr ◽  
Pechmann Condensation ◽  
Solvent Free Conditions ◽  
Ft Ir ◽  
C Nmr

A nitro coumarin derivatives has been synthesized via nitration of 7-hydroxy-4-methyl coumarin wich was synthesized via Pechmann condensation resorcinol with a β-ketoester using Amberlyst-15 as a green and efficient catalyst and by caring out the reaction of resorcinol and ethyl acetoacetate (with 1: 1 mol ratio) in the presence of 0.2 g of Amberlyst-15 at 110°C under solvent-free conditions. These nitro coumarin derivatives have biological activity and momentousness in the industrial fields. The purified products were measured the melting points and characterized by spectral methods: FT-IR,1H-NMR ,13C-NMR.

Hafnium(IV) Chloride Catalyzes Highly Efficient Acetalization of Carbonyl Compounds

2019 ◽  
Vol 16 (6) ◽  
pp. 913-920 ◽  
Author(s):  
Israel Bonilla-Landa ◽  
Emizael López-Hernández ◽  
Felipe Barrera-Méndez ◽  
Nadia C. Salas ◽  
José L. Olivares-Romero
Keyword(s):  
Microwave Heating ◽  
Reaction Times ◽  
Protecting Groups ◽  
Catalyst Loading ◽  
Selective Protection ◽  
Highly Efficient ◽  
Aldehydes And Ketones ◽  
High Yields ◽  
Novel Catalyst ◽  
Acid Labile

Background: Hafnium(IV) tetrachloride efficiently catalyzes the protection of a variety of aldehydes and ketones, including benzophenone, acetophenone, and cyclohexanone, to the corresponding dimethyl acetals and 1,3-dioxolanes, under microwave heating. Substrates possessing acid-labile protecting groups (TBDPS and Boc) chemoselectively generated the corresponding acetal/ketal in excellent yields. Aim and Objective: In this study. the selective protection of aldehydes and ketones using a Hafnium(IV) chloride, which is a novel catalyst, under microwave heating was observed. Hence, it is imperative to find suitable conditions to promote the protection reaction in high yields and short reaction times. This study was undertaken not only to find a novel catalyst but also to perform the reaction with substrates bearing acid-labile protecting groups, and study the more challenging ketones as benzophenone. Materials and Methods: Using a microwave synthesis reactor Monowave 400 of Anton Paar, the protection reaction was performed on a raging temperature of 100°C ±1, a pressure of 2.9 bar, and an electric power of 50 W. More than 40 substrates have been screened and protected, not only the aldehydes were protected in high yields but also the more challenging ketones such as benzophenone were protected. All the products were purified by simple flash column chromatography, using silica gel and hexanes/ethyl acetate (90:10) as eluents. Finally, the protected substrates were characterized by NMR 1H, 13C and APCI-HRMS-QTOF. Results: Preliminary screening allowed us to find that 5 mol % of the catalyst is enough to furnish the protected aldehyde or ketone in up to 99% yield. Also it was found that substrates with a variety of substitutions on the aromatic ring (aldehyde or ketone), that include electron-withdrawing and electrondonating group, can be protected using this methodology in high yields. The more challenging cyclic ketones were also protected in up to 86% yield. It was found that trimethyl orthoformate is a very good additive to obtain the protected acetophenone. Finally, the protection of aldehydes with sensitive functional groups was performed. Indeed, it was found that substrates bearing acid labile groups such as Boc and TBDPS, chemoselectively generated the corresponding acetal/ketal compound while keeping the protective groups intact in up to 73% yield. Conclusion: Hafnium(IV) chloride as a catalyst provides a simple, highly efficient, and general chemoselective methodology for the protection of a variety of structurally diverse aldehydes and ketones. The major advantages offered by this method are: high yields, low catalyst loading, air-stability, and non-toxicity.

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.

Studies on electrooxidation of lignin and lignin model compounds. Part 1: Direct electrooxidation of non-phenolic lignin model compounds

Holzforschung ◽  
2012 ◽  
Vol 66 (3) ◽  
Author(s):  
Takumi Shiraishi ◽  
Toshiyuki Takano ◽  
Hiroshi Kamitakahara ◽  
Fumiaki Nakatsubo
Keyword(s):  
Electron Transfer ◽  
Cyclic Voltammetry ◽  
Carbonyl Compounds ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Bulk Electrolysis ◽  
Lignin Model ◽  
Dimeric Compound ◽  
High Yields ◽  
Short Time

Abstract The direct anodic oxidation of non-phenolic lignin model compounds was investigated to understand their basic behaviors. The results of cyclic voltammetry (CV) studies of monomeric model, such as 1-(4-ethoxy-3-methoxyphenyl)ethanol, are interpreted as the oxidation for Cα-carbonylation did not proceed in the reaction without a catalyst, but a base promotes this reaction. Indeed, the bulk electrolyses of the monomeric lignin model compounds with 2,6-lutidine afforded the corresponding Cα-carbonyl compounds in high yields (60–80%). It is suggested that deprotonation at Cα-H in the ECEC mechanism (E=electron transfer and C=chemical step) is important for Cα-carbonylation. In the uncatalyzed bulk electrolysis of a β-O-4 model dimeric compound, 4-ethoxy-3-methoxyphenylglycerol-β-guaiacyl ether, the corresponding Cα-carbonyl compound was not detected but as a result of Cα-Cβcleavage 4-O-ethylvanillin was found in 40% yield. In the electrolysis reaction in the presence of 2,6-lutidine (as a sterically hindered light base), the reaction stopped for a short time unexpectedly. These results indicate the different electrochemical behavior of simple monomeric model compounds and dimeric β-O-4 models. The conclusion is that direct electrooxidation is unsuitable for Cα-carbonylation of lignin.

Hypervalent iodine catalysis for selective oxidation of Baylis–Hillman adducts via in situ generation of o-iodoxybenzoic acid (IBX) from 2-iodosobenzoic acid (IBA) in the presence of oxone

2016 ◽  
Vol 40 (12) ◽  
pp. 10300-10304 ◽  
Author(s):  
Raktani Bikshapathi ◽  
Parvathaneni Sai Prathima ◽  
Vaidya Jayathirtha Rao
Keyword(s):  
Selective Oxidation ◽  
Carbonyl Compounds ◽  
Hypervalent Iodine ◽  
In Situ Generation ◽  
Iodosobenzoic Acid ◽  
High Yields

An efficient, eco-friendly protocol for selective oxidation of primary and secondary Baylis–Hillman alcohols to the corresponding carbonyl compounds in high yields has been developed with 2-iodosobenzoic acid (IBA).

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