Chitosan: A Natural and Sustainable Polymeric Organocatalyst for C-C Bond Formation During the Synthesis of 5-amino-2,3-dihydrobenzo[d] thiazole-4,6-dicarbonitriles

2019 ◽  
Vol 6 (1) ◽  
pp. 69-76
Author(s):  
Km N. Shivhare ◽  
Ibadur R. Siddiqui
Keyword(s):  
Catalytic Activity ◽  
Multicomponent Reaction ◽  
Bond Formation ◽  
Environmentally Benign ◽  
One Pot ◽  
Reaction Condition ◽  
Three Component Reaction ◽  
Efficient Route

Background: A green, recyclable and reusable chitosan catalyst has been utilized for the synthesis of 5-amino-2,3-dihydrobenzo[d]thiazole-4,6-dicarbonitrile and its derivatives. Methods and Results: Three-component reaction protocol incorporates the reaction of aldehydes, malononitrile and rhodanine derivatives. This is examined as an efficient route for the synthesis of dicarbonitriles utilizing a green, biodegradable, environmentally benign, and easily available chitosan catalyst. In the reported protocol, catalyst can be recycled and not any substantial dropping in its catalytic activity during the recycling steps was obtained. Conclusion: A green and environmentally benign, one pot three-component protocol has been illustrated for the synthesis of 5-amino-2,3-dihydrobenzo[d]thiazole-4,6-dicarbonitrile derivatives. Adequately yield products were gained via the natural catalytic approach with the recyclability of the catalyst. The use of chitosan represents this procedure as an attractive substitute for the synthesis of biaryls complex by multicomponent reaction condition.

scholarly journals Synthesis of tetrazolo[1,5-a]pyrimidine-6-carbonitriles using HMTA-BAIL@MIL-101(Cr) as a superior heterogeneous catalyst

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Mohammad Hossein Abdollahi-Basir ◽  
Boshra Mirhosseini-Eshkevari ◽  
Farzad Zamani ◽  
Mohammad Ali Ghasemzadeh
Keyword(s):  
Ionic Liquid ◽  
Catalytic Activity ◽  
Reaction Time ◽  
Metal Organic Framework ◽  
One Pot ◽  
Short Reaction Time ◽  
Three Component Reaction ◽  
Metal Organic ◽  
Ft Ir ◽  
Novel Catalyst

AbstractA one-pot three component reaction of benzaldehydes, 1H-tetrazole-5-amine, and 3-cyanoacetyl indole in the presence of a new hexamethylenetetramine-based ionic liquid/MIL-101(Cr) metal–organic framework as a recyclable catalyst was explored. This novel catalyst, which was fully characterized by XRD, FE-SEM, EDX, FT-IR, TGA, BET, and TEM exhibited outstanding catalytic activity for the preparation of a range of pharmaceutically important tetrazolo[1,5-a]pyrimidine-6-carbonitriles with good to excellent yields in short reaction time.

scholarly journals Cu(II) and magnetite nanoparticles decorated melamine-functionalized chitosan: A synergistic multifunctional catalyst for sustainable cascade oxidation of benzyl alcohols/Knoevenagel condensation

2019 ◽  
Vol 9 (1) ◽  
Author(s):  
Zahra Alirezvani ◽  
Mohammad G. Dekamin ◽  
Ehsan Valiey
Keyword(s):  
Catalytic Activity ◽  
Knoevenagel Condensation ◽  
Ambient Pressure ◽  
Reaction Medium ◽  
Environmentally Benign ◽  
One Pot ◽  
Benzyl Alcohols ◽  
External Magnet ◽  
Multistep Synthesis ◽  
Multifunctional Catalyst

AbstractThe uniform decoration of Cu(II) species and magnetic nanoparticles on the melamine-functionalized chitosan afforded a new supramolecular biopolymeric nanocomposite (Cs-Pr-Me-Cu(II)-Fe3O4). The morphology, structure, and catalytic activity of the Cs-Pr-Me-Cu(II)-Fe3O4 nanocomposite have been systematically investigated. It was found that Cs-Pr-Me-Cu(II)-Fe3O4 nanocomposite can smoothly promote environmentally benign oxidation of different benzyl alcohol derivatives by tert-butyl hydroperoxide (TBHP) to their corresponding benzaldehydes and subsequent Knoevenagel condensation with malononitrile, as a multifunctional catalyst. Interestingly, Fe3O4 nanoparticles enhance the catalytic activity of Cu(II) species. The corresponding benzylidenemalononitriles were formed in high to excellent yields at ambient pressure and temperature. The heterogeneous Cs-Pr-Me-Cu(II)-Fe3O4 catalyst was also very stable with almost no leaching of the Cu(II) species into the reaction medium and could be easily recovered by an external magnet. The recycled Cs-Pr-Me-Cu(II)-Fe3O4 was reused at least four times with slight loss of its activity. This is a successful example of the combination of chemo- and bio-drived materials catalysis for mimicing biocatalysis as well as sustainable and one pot multistep synthesis.

Fast and Efficient Green Procedure for the Synthesis of Benzo[5,6]chromene Derivatives and Their Sulfur Analogues in Water by Organocatalyst Potassium Phthalimide-N-oxyl

Synthesis ◽  
2020 ◽  
Vol 52 (11) ◽  
pp. 1707-1718
Author(s):  
Nasser Etivand ◽  
Jabbar Khalafy ◽  
Mohammad G. Dekamin
Keyword(s):  
Aqueous Media ◽  
Thiobarbituric Acid ◽  
Environmentally Benign ◽  
The Novel ◽  
One Pot ◽  
Synthetic Strategy ◽  
Three Component Reaction ◽  
High Yields ◽  
Green Procedure ◽  
Arylglyoxal Monohydrates

A simple, clean, straightforward, and environmentally benign one-pot, three-component reaction of various arylglyoxal monohydrates, β-naphthol, and barbituric acid [pyrimidine-2,4,6(1H,3H,5H)-trione] or thiobarbituric acid in the presence of catalytic amounts potassium phthalimide-N-oxyl (PPINO), as a mild and efficient organocatalyst in aqueous media under reflux conditions is reported. This transformation produced the novel diverse-substituted 12-benzoyl-8,12-dihydro-9H-benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H)-diones and their sulfur analogues in 82–93% yield via filtration and without utilization of any chromatography. The high yields of products, very simple operation, easy workup, availability of starting materials, green process, and high atom-economy are the main benefits of this synthetic strategy.

CuI/Et2NH-Catalyzed One-Pot Highly Efficient Synthesis of 1,4-Disubstituted 1,2,3-Triazoles in Green Solvent Glycerol

Synthesis ◽  
2018 ◽  
Vol 50 (11) ◽  
pp. 2191-2199 ◽  
Author(s):  
Yongde Zhao ◽  
Shengqiang Guo ◽  
Yang Zhou ◽  
Bencai Dai ◽  
Cuimeng Huo ◽  
...  
Keyword(s):  
Catalytic System ◽  
Sodium Azide ◽  
Room Temperature ◽  
Green Solvent ◽  
Efficient Synthesis ◽  
One Pot ◽  
Highly Efficient ◽  
Three Component Reaction ◽  
Efficient Route ◽  
Terminal Acetylenes

A concise one-pot three-component reaction of organic halides­, terminal acetylenes, and sodium azide provided an efficient route for the synthesis of 1,2,3-triazoles. A variety of 1,2,3-triazoles were prepared in good to excellent yields with green solvent glycerol. This procedure used CuI and diethylamine, which are two easily available reagents as the new catalytic system at room temperature.

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 N-Methylphthalimide-substituted benzimidazolium salts and PEPPSI Pd–NHC complexes: synthesis, characterization and catalytic activity in carbon–carbon bond-forming reactions

2016 ◽  
Vol 12 ◽  
pp. 81-88 ◽  
Author(s):  
Senem Akkoç ◽  
Yetkin Gök ◽  
İlhan Özer İlhan ◽  
Veysel Kayser
Keyword(s):  
Catalytic Activity ◽  
Bond Formation ◽  
Carbene Complexes ◽  
Bond Forming ◽  
H Nmr ◽  
Fticr Ms ◽  
Carbon Carbon Bond ◽  
Efficient Route ◽  
Good Catalytic Activity ◽  
Benzimidazolium Salts

A series of novel benzimidazolium salts (1–4) and their pyridine enhanced precatalyst preparation stabilization and initiation (PEPPSI) themed palladium N-heterocyclic carbene complexes [PdCl2(NHC)(Py)] (5–8), where NHC = 1-(N-methylphthalimide)-3-alkylbenzimidazolin-2-ylidene and Py = 3-chloropyridine, were synthesized and characterized by means of 1H and 13C{1H} NMR, UV–vis (for 5–8), ESI-FTICR-MS (for 2, 4, 6–8) and FTIR spectroscopic methods and elemental analysis. The synthesized compounds were tested in Suzuki–Miyaura cross-coupling (for 1–8) and arylation (for 5–8) reactions. As catalysts, they demonstrated a highly efficient route for the formation of asymmetric biaryl compounds even though they were used in very low loading. For example, all compounds displayed good catalytic activity for the C–C bond formation of 4-tert-butylphenylboronic acid with 4-chlorotoluene.

scholarly journals One-pot multicomponent synthesis of highly substituted pyridines using hydrotalcite as a solid base and reusable catalyst

2021 ◽  
pp. 169-174
Author(s):  
Sandip R. Kale ◽  
Santosh Kumar Surve
Keyword(s):  
Catalytic Activity ◽  
Multicomponent Reaction ◽  
Aromatic Aldehydes ◽  
Significant Loss ◽  
Solid Base ◽  
Reusable Catalyst ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
One Pot Synthesis ◽  
Substituted Pyridines

One-pot synthesis of highly substituted pyridines has been demonstrated via multicomponent reaction of aldehydes, malononitrile and thiophenol using Mg-Al hydrotalcite as a solid base and reusable catalyst. The catalytic activity is intimately connected to the basicity of the catalyst. The best activities were observed with the Mg/Al: 5 catalyst. The catalyst could be reused for further run without a significant loss in activity. The protocol was also applicable for various aromatic aldehydes which affords desired product in good to excellent yield.

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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