One-Pot Three-Component Reaction of C60, Amino Acid and Fluorinated Benzaldehyde to C60-Pyrrolidine Derivatives.

AbstractAn efficient, one-pot, three-component [3+2] cycloaddition reaction of azomethine ylide obtained from α-dicarbonyl compounds (cyclic and acyclic diketone or keto ester) and amino acids with maleimides under catalyst-free conditions has been developed. This cascade protocol shows high efficiency and remarkable functional group tolerance, and the ubiquitous succinimide-fused pyrrolizidines with a highly compact and strained scaffold were obtained with high yield and excellent diastereoselectivity. Furthermore, this novel and atom-economical strategy could be performed on a gram scale with comparable reaction efficiency.

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Synthesis of a novel category of pseudo-peptides using an Ugi three-component reaction of levulinic acid as bifunctional substrate, amines, and amino acid-based isocyanides

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.15.82 ◽

2019 ◽

Vol 15 ◽

pp. 852-857 ◽

Cited By ~ 4

Author(s):

Maryam Khalesi ◽

Azim Ziyaei Halimehjani ◽

Jürgen Martens

Keyword(s):

Amino Acid ◽

Functional Groups ◽

Levulinic Acid ◽

Ugi Reaction ◽

Aliphatic Amines ◽

One Pot ◽

Heterocyclic Molecules ◽

Three Component Reaction ◽

Aromatic And Aliphatic Amines

The synthesis of a novel category of pseudo-peptides via intramolecular Ugi reaction of levulinic acid (4-oxopentanoic acid), aromatic and aliphatic amines, and amino acid-based isocyanides is reported. Levulinic acid was applied as a bifunctional substrate containing both carbonyl and acid moieties suitable for the Ugi reaction. This article provides a facile and convenient one-pot procedure for the synthesis of peptide-like heterocyclic molecules containing 2-pyrrolidone (γ-lactam), amide and ester functional groups with good to excellent yields.

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One-pot three-component reaction of C60, amino acid and fluorinated benzaldehyde to C60-pyrrolidine derivatives

Journal of Fluorine Chemistry ◽

10.1016/j.jfluchem.2004.12.018 ◽

2005 ◽

Vol 126 (3) ◽

pp. 349-353 ◽

Cited By ~ 10

Author(s):

Sheng Wang ◽

Jian-min Zhang ◽

Li-ping Song ◽

Hu Jiang ◽

Shi-zheng Zhu

Keyword(s):

Amino Acid ◽

One Pot ◽

Three Component Reaction

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Metal-, and Organocatalyst-Free One-Pot Assembly of Chiral Aza-Tricyclic Molecules: Creating Six Contiguous Stereocenters from 2-D-Structures and an Amino Acid

10.26434/chemrxiv.12757943.v1 ◽

2020 ◽

Author(s):

Dung Do

Keyword(s):

Amino Acid ◽

Chemical Space ◽

Structural Diversity ◽

Therapeutic Agents ◽

Chiral Molecules ◽

One Pot ◽

Complex Molecules ◽

Chiral Catalyst ◽

Chiral Complex ◽

Free Process

<p>Chiral molecules with their defined 3-D structures are of paramount importance for the study of chemical biology and drug discovery. Having rich structural diversity and unique stereoisomerism, chiral molecules offer a large chemical space that can be explored for the design of new therapeutic agents.<sup>1</sup> Practically, chiral architectures are usually prepared from organometallic and organocatalytic processes where a transition metal or an organocatalyst is tailor-made for desired reactions. As a result, developing a method that enables rapid assembly of chiral complex molecules under metal- and organocatalyst-free condition represents a daunting challenge. Here we developed a straightforward route to create a chiral 3-D structure from 2-D structures and an amino acid without any chiral catalyst. The center of this research is the design of a <a>special chiral spiroimidazolidinone cyclohexadienone intermediate</a>, a merger of a chiral reactive substrate with multiple nucleophillic/electrophillic sites and a transient organocatalyst. <a>This unique substrate-catalyst (“subcatalyst”) dual role of the intermediate enhances </a><a>the coordinational proximity of the chiral substrate and catalyst</a> in the key Aza-Michael/Michael cascade resulting in a substantial steric discrimination and an excellent overall diastereoselectivity. Whereas the “subcatalyst” (hidden catalyst) is not present in the reaction’s initial components, which renders a chiral catalyst-free process, it is strategically produced to promote sequential self-catalyzed reactions. The success of this methodology will pave the way for many efficient preparations of chiral complex molecules and aid for the quest to create next generation of therapeutic agents.</p>

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Novel One-pot Synthesis of Pyranocarbazole Derivatives via an Isocyanide-based Three-component Reaction

Letters in Organic Chemistry ◽

10.2174/1570178617999201020215852 ◽

2020 ◽

Vol 17 ◽

Author(s):

Visarapu Malathi ◽

Pedavenkatagari Narayana Reddy ◽

Pannala Padmaja

Keyword(s):

Efficient Method ◽

Atom Economy ◽

Reaction Conditions ◽

One Pot ◽

Catalyst Free ◽

One Pot Synthesis ◽

Three Component Reaction ◽

High Yields

Abstract:: An efficient method has been developed for the synthesis of new pyrano[3,2-c] and pyrano[3,2-a]carbazole de-rivatives via a three component reaction of 4-hydroxycarbazole or 2-hydroxycarbazole, isocyanides, and dialkylacetylenedi-carboxylates. Noteworthy features of this protocol include mild reaction conditions, catalyst-free, high atom-economy and high yields.

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Design, Synthesis, In vitro Cytotoxic Activity Evaluation, and Study of Apoptosis Inducing Effect of New Styrylimidazo[1,2-a]Pyridines as Potent Anti-Breast Cancer Agents

Anti-Cancer Agents in Medicinal Chemistry ◽

10.2174/1871520618666180903100835 ◽

2019 ◽

Vol 19 (2) ◽

pp. 265-275 ◽

Cited By ~ 2

Author(s):

Faeze Khalili ◽

Sara Akrami ◽

Malihe Safavi ◽

Maryam Mohammadi-Khanaposhtani ◽

Mina Saeedi ◽

...

Keyword(s):

Breast Cancer ◽

Cytotoxic Activity ◽

High Yield ◽

Breast Cancer Cell Lines ◽

Pyridine Derivatives ◽

One Pot ◽

Standard Drug ◽

Three Component Reaction ◽

Anti Cancer

Background: This paper reports synthesis, cytotoxic activity, and apoptosis inducing effect of a novel series of styrylimidazo[1,2-a]pyridine derivatives. Objective: In this study, anti-cancer activity of novel styrylimidazo[1,2-a]pyridines was evaluated. Methods: Styrylimidazo[1,2-a]pyridine derivatives 4a-o were synthesized through a one-pot three-component reaction of 2-aminopyridines, cinnamaldehydes, and isocyanides in high yield. All synthesized compounds 4a-o were evaluated against breast cancer cell lines including MDA-MB-231, MCF-7, and T-47D using MTT assay. Apoptosis was evaluated by acridine orange/ethidium bromide staining, cell cycle analysis, and TUNEL assay as the mechanism of cell death. Results: Most of the synthesized compounds exhibited more potent cytotoxicity than standard drug, etoposide. Induction of apoptosis by the most cytotoxic compounds 4f, 4g, 4j, 4n, and 4m was confirmed through mentioned methods. Conclusion: In conclusion, these results confirmed the potency of styrylimidazo[1,2-a]pyridines for further drug discovery developments in the field of anti-cancer agents.

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One-Pot Three Component Synthesis of 2-(1H-Benzo[d]thiazole-2-yl)- N-Arylbenzamides in Glycerol Medium

Asian Journal of Chemistry ◽

10.14233/ajchem.2020.22538 ◽

2020 ◽

Vol 32 (6) ◽

pp. 1343-1351

Author(s):

Swathi Thumula ◽

Venkatesan Srinivasadesikan ◽

Ravi K. Kottalanka ◽

S. Rex Jeya Rajkumar ◽

Balajee Ramchandran

Keyword(s):

Docking Study ◽

Molecular Docking Study ◽

One Pot ◽

Docking Result ◽

Three Component Reaction ◽

Antibacterial Target ◽

Short Time ◽

A549 Lung ◽

Glycerol Medium ◽

Mcf 7

In this work, a series of 2-(1H-benzo[d]thiazole-2-yl)-N-arylbenzamides is synthesized by using diethyl phthalate, anilines and 2-amino-benzenethiol by one-pot three component synthesis in glycerol medium. Phosphoric acid is used as an effective reagent for this one-pot three component reaction. This reaction got completed in a short time, easy workup and gave an excellent yield in glycerol medium. The N-arylbenzamides was found to have significant cytotoxic potentials against various cancer cells viz., A549 (lung cancer), HeLa (cervical cancer) and MCF-7 (breast cancer) using MTT assay. The molecular docking study is also employed to understand the binding mechanism of N-arylbenzamides against the antibacterial target. The docking result shows the binding energy of compound 4a is -8.6 kcal/mol. The binding affinity is a major concern and it shows that Asn and Thr residues have an interaction with compound 4a.

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

Scientific Reports ◽

10.1038/s41598-021-84379-3 ◽

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.

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Catalyst- and solvent-free Csp2-H functionalization of 4-hydroxycoumarins via C-3 dehydrogenative aza-coupling under ball-milling

Green Chemistry ◽

10.1039/d1gc01341f ◽

2021 ◽

Author(s):

Goutam Brahmachari ◽

Indrajit Karmakar ◽

Pintu Karmakar

Keyword(s):

Ball Milling ◽

Aromatic Amines ◽

Solvent Free ◽

One Pot ◽

Biologically Relevant ◽

Tert Butyl ◽

Three Component Reaction ◽

Primary Aromatic Amines

A one-pot procedure for the synthesis of biologically relevant coumarin-hydrazones by a three-component reaction between 4-hydrocoumarins, primary aromatic amines and tert-butyl nitrite under ball-milling in the absence of any catalyst/additive...

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Clean one-pot multicomponent synthesis of pyrans using a green and magnetically recyclable heterogeneous nanocatalyst

SynOpen ◽

10.1055/a-1469-6721 ◽

2021 ◽

Author(s):

Mina Ghassemi ◽

Ali Maleki

Keyword(s):

Room Temperature ◽

Significant Loss ◽

Copper Ferrite ◽

Multicomponent Synthesis ◽

Thermo Gravimetric ◽

Sem Images ◽

One Pot ◽

Three Component Reaction ◽

Ft Ir ◽

The One

Copper ferrite (CuFe2O4) magnetic nanoparticles (MNPs) were synthesized via thermal decomposition method and applied as a reusable and green catalyst in the synthesis of functionalized 4H-pyran derivatives using malononitrile, an aromatic aldehyde and a β-ketoester in ethanol at room temperature. Then it was characterized by Fourier transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX) analysis, scanning electron microscopy (SEM) images, thermo gravimetric and differential thermo gravimetric (TGA/DTG) analysis. The catalyst was recovered from the reaction mixture by applying an external magnet and decanting the mixture. Recycled catalyst was reused for several times without significant loss in its activity. Running the one-pot three-component reaction at room temperature, no use of eternal energy source and using a green solvent provide benign, mild, and environmentally friendly reaction conditions; as well, ease of catalyst recovering, catalyst recyclability, no use of column chromatography and good to excellent yields are extra advantages of this work.

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