Assembly of N,N-disubstituted-N′-arylureas via a copper-catalyzed one-pot three-component reaction of aryl bromides, potassium cyanate, and secondary amines

Tetrahedron ◽  
2013 ◽  
Vol 69 (26) ◽  
pp. 5326-5330 ◽  
Author(s):  
Hongfei Yin ◽  
Bing Chen ◽  
Xiaojing Zhang ◽  
Xinye Yang ◽  
Yihua Zhang ◽  
...  
Keyword(s):  
Secondary Amines ◽  
One Pot ◽  
Aryl Bromides ◽  
Three Component Reaction

scholarly journals Synthesis, Characterization and Anticancer Evaluation of Nitrogen Substituted 1-(3-Aminoprop-1-ynyl)-4-Hydroxyanthraquinone Derivatives

2021 ◽  
Author(s):  
Nafisa S. Sirazhetdinova ◽  
Dmitry S Baev ◽  
Victor A. Savelyev ◽  
Tatyana S. Golubeva ◽  
Lyubov S. Klimenko ◽  
...  
Keyword(s):  
Cancer Cells ◽  
Sonogashira Reaction ◽  
Secondary Amines ◽  
One Pot ◽  
Standard Drug ◽  
Three Component Reaction ◽  
G Quadruplex ◽  
New Compounds ◽  
Substituted 1 ◽  
Mcf 7

Abstract Anthraquinones are of significant interest due to their biological activity, coloring properties and synthetic applications. Here, we describe a mild and convenient method for modification of 1-ethynyl-4-hydroxyanthraquinone that was obtained from the Sonogashira reaction of 1-hydroxy-4-iodoanthraquinone with alkynes. The copper(I) catalyzed one-pot three component reaction (A3-coupling) of the new 1-ethynyl-4-hydroxyanthraquinone with secondary amines and formaldehyde was the main approach for the synthesis of nitrogen substituted 1-[3-(amino)prop-1-ynyl]-4-hydroxyanthraquinones. The influence of different substituent in the amine on reaction rate and yield has been evaluated. The cytotoxicity of 1-ethynyl-4-hydroxyanthraquinones was evaluated using the conventional MTT assay. Among all the compounds synthesized, anthraquinone-propargylamine derivatives 28, 29, 30 and 34 possess most promising cytotoxic potential towards glioblastoma cancer cells; compounds 14 and 19 shown selectivity towards the prostate cancer cells DU-145, and 18, and 24 – towards breast cancer cells MCF-7. The grown inhibition on these cancer cells of 18 and 24 was comparable to those of standard drug Doxorubicin. Molecular modeling of new compounds in DNA G-quadruplex binding site was performed to help understand the observed SAR trends.

One-pot synthesis of 3-aminofurans using a simple and efficient recyclable CuI/[bmim]PF6 system

2021 ◽  
Author(s):  
Guguloth Veeranna ◽  
Ramesh Balaboina ◽  
Narasimha Swamy Thirukovela ◽  
Ravindhar Vadde
Keyword(s):  
Secondary Amines ◽  
Terminal Alkynes ◽  
One Pot ◽  
One Pot Synthesis ◽  
System P ◽  
Three Component Reaction ◽  
The One

The one-pot three-component reaction of several 2-ketoaldehdyes, secondary amines and terminal alkynes to access 3-aminofurans was proceeded well in [bmim][PF6] using a simple and cheap CuI catalyst. The resulted 3-aminofuran...

The Discovery of Ultrasound Irradiation as a Useful Tool for Accelerating Petasis Three-component Reaction: Synthesis of α-Arylglycines

2018 ◽  
Vol 15 (2) ◽  
pp. 256-266 ◽  
Author(s):  
Fan Yun ◽  
Chunhui Cheng ◽  
Jingxuan Li ◽  
Pingwah Tang ◽  
Qipeng Yuan
Keyword(s):  
Reaction Time ◽  
Glyoxylic Acid ◽  
Reaction Times ◽  
Ultrasound Irradiation ◽  
Secondary Amines ◽  
One Pot ◽  
Petasis Reaction ◽  
Three Component Reaction ◽  
Wide Range ◽  
High Yields

Aim and Objective: α-Arylglycines belong to an important class of non-proteinogenic amino acids. Petasis 3-component, one-pot reaction lends itself to be suitable for the synthesis of α-Arylglycines. Because of the low reactivity, Petasis reaction requires long reaction time. Our objective is to use ultrasound irradiation to accelerate this versatile Petasis' synthesis of α-Arylglycines. Materials and Methods: Ultrasound irradiation as a physical tool to accelerate the Petasis 3-component reaction without any auxiliary catalyst can significantly shorten the reaction time. The operation is simple. It can be applied to a wide range of substrates. In order to highlight the remarkable utility of the ultrasound in Petasis reaction, we have compared side-by-side the reactivity between the reaction with ultrasound and the one without ultrasound. Results: Using ultrasound, the reaction times of Petasis reactions with various amine substrates including primary and secondary amines, heterocyclic amines, with a wide variety of boronic acids having different substituents (activating and deactivating groups) in the phenyl rings, and with glyoxylic acid and salicylic aldehyde were shortened from 5 to more than 20-fold. Conclusion: We have discovered the first examples of an efficient ultrasound-promoted approach for Petasis reaction to prepare a series of α-arylglycines in high yields and in excellent purities. The low reactivity of the reactions in this study were significantly enhanced by the ultrasound irradiation. By virtue of the acceleration and the operational simplicity, the present ultrasound assisted Petasis reaction can find applications in the synthetic areas of the already widely used Petasis three-component reaction.

scholarly journals ZnO Catalyzed Efficient Synthesis of Some New 2-Substituted-4,6-diarylpyrimidines

2012 ◽  
Vol 2012 ◽  
pp. 1-6
Author(s):  
K. L. Ameta ◽  
Biresh Kumar ◽  
Nitu S. Rathore
Keyword(s):  
Reaction Time ◽  
Heterogeneous Catalyst ◽  
Simple Procedure ◽  
Secondary Amines ◽  
Efficient Synthesis ◽  
One Pot ◽  
Short Reaction Time ◽  
Three Component Reaction

A simple and efficient protocol is developed for the synthesis of 2-substituted-4,6-diarylpyrimidines from one-pot three-component reaction of 4′-hydroxy-3′,5′-dinitro substituted chalcones, S-benzylthiouronium chloride (SBT), and heterocyclic secondary amines (morpholine/pyrrolidine/piperidine) in the presence of 15 mol% of ZnO as a heterogeneous catalyst. The present methodology offers several advantages such as being a simple procedure as well as providing excellent yields, and short reaction time. The catalyst is inexpensive, stable, and can be easily recycled and reused for several cycles with consistent activity.

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

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.

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

2019 ◽  
Vol 19 (2) ◽  
pp. 265-275 ◽  
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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