Diversity oriented multi-component reaction (DOS–MCR) approach to access natural product analogues: regio- and chemo-selective synthesis of polyheterocyclic scaffolds via one-pot cascade reactions

2020 ◽  
Vol 18 (16) ◽  
pp. 3082-3092
Author(s):  
Lakshmanan Palanivel ◽  
Vasuki Gnanasambandam
Keyword(s):  
Natural Product ◽  
Cascade Reactions ◽  
Selective Synthesis ◽  
One Pot ◽  
Diversity Oriented Synthesis ◽  
Three Component Reaction ◽  
Couple Pair ◽  
Hybrid Scaffolds

Skeletally diverse and complex polyheterocyclic hybrid scaffolds have been accessed via one-pot three-component reaction by exploiting the build/couple/pair strategy of diversity oriented synthesis.

A Simple and Efficient Diversity-Oriented Synthesis of New Substituted 3-(Arylamino)-6,7-dihydro-1H-indazol-4(5H)-ones by a KOH-Assisted One-Pot Reaction

2017 ◽  
Vol 70 (12) ◽  
pp. 1274 ◽  
Author(s):  
Mehdi Rimaz ◽  
Behzad Khalili ◽  
Golaleh Khatyal ◽  
Hossein Mousavi ◽  
Farkhondeh Aali
Keyword(s):  
Aprotic Solvent ◽  
Combinatorial Method ◽  
Reaction Conditions ◽  
One Pot ◽  
Diversity Oriented Synthesis ◽  
Synthetic Strategy ◽  
Polar Aprotic Solvent ◽  
Three Component Reaction ◽  
Aromatic Isothiocyanates ◽  
Operational Simplicity

A novel, simple, and straightforward combinatorial method for the synthesis of new substituted 3-(arylamino)-6,7-dihydro-1H-indazol-4(5H)-one derivatives has been developed. The synthesis was achieved via a one-pot three-component reaction of aromatic isothiocyanates, substituted 1,3-cyclohexanediones, and hydrazine hydrate in dimethyl sulfoxide as a polar aprotic solvent. This methodology has the advantages of mild reaction conditions, good to excellent yields, easily available starting materials, operational simplicity, and easy workup. This chemistry provides an efficient synthetic strategy to diversity-oriented construction of the 3-arylaminoindazole skeleton.

Diversity-Oriented Synthesis of Spiro-Substituted 1,3-Thiazine Library via a One-Pot, Two-Step, Three-Component Reaction

2010 ◽  
Vol 13 (1) ◽  
pp. 84-88 ◽  
Author(s):  
Qi-Ya Zhuang ◽  
Xiang Wang ◽  
Yuan Gao ◽  
Feng Shi ◽  
Bo Jiang ◽  
...  
Keyword(s):  
One Pot ◽  
Diversity Oriented Synthesis ◽  
Three Component Reaction

Highly selective synthesis of 1-polyfluoroaryl-1,2,3-triazoles via a one-pot three-component reaction

2014 ◽  
Vol 55 (36) ◽  
pp. 5033-5037 ◽  
Author(s):  
Liming Cao ◽  
Cuibo Liu ◽  
Xiangyang Tang ◽  
Xuguang Yin ◽  
Bin Zhang
Keyword(s):  
Selective Synthesis ◽  
One Pot ◽  
Three Component Reaction

scholarly journals Diversity-Oriented Synthesis of Novel Trihalomethyl-Containing Spirochromeno[3,4-a](thia)pyrrolizidines and Spirochromeno-[3,4-a]indolizidines by One-Pot, Three-Component [3+2]-Cyclo­addition Reaction

SynOpen ◽  
2021 ◽  
Vol 05 (01) ◽  
pp. 1-16
Author(s):  
Vladislav Y. Korotaev ◽  
Igor B. Kutyashev ◽  
Maxim S. Sannikov ◽  
Ivan A. Kochnev ◽  
Alexey Y. Barkov ◽  
...  
Keyword(s):  
Azomethine Ylides ◽  
X Ray Diffraction ◽  
One Pot ◽  
Relative Configuration ◽  
Diversity Oriented Synthesis ◽  
X Ray ◽  
2D Noesy ◽  
Three Component Reaction ◽  
Trifluoromethyl Groups

AbstractRegio- and stereoselective methods for the synthesis of 6′-trifluoro(trichloro)methyl substituted spiro[acenaphthylene-1,11′-chromeno[3,4-a](thia)pyrrolizidin]-2-ones and spiro[acenaphthylene-1,12′-chromeno[3,4-a]indolizidin]-2-ones have been developed based on the three-component reaction of 3-nitro-2-trifluoro(trichloro)methyl-2H-chromenes with azomethine ylides generated in situ from acenaphthenequinone and cyclic α-amino acids. The cycloaddition proceeds under mild conditions in ethanol or DMSO, and only endo-isomers of the products with cis-arrangement of nitro and trifluoromethyl groups are formed. The relative configuration of cycloadducts is reliably confirmed by X-ray diffraction analysis and by 2D NOESY spectroscopy.

A One-Pot Chemoenzymatic Synthesis of (2S,4R)-4-Methylproline Enables the First Total Synthesis of Antiviral Lipopeptide Cavinafungin B

2018 ◽  
Author(s):  
Christian R. Zwick ◽  
Hans Renata
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Complex Molecule ◽  
Molecular Target ◽  
Chemoenzymatic Synthesis ◽  
General Strategy ◽  
One Pot

We report an efficient ten-step synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (Rink-Boc-ATG-resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner.This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.

Metal-Free Photoredox-Catalyzed C–H/C–H Coupling of Arenes Enabled by Interrupted Pummerer Activation

2019 ◽  
Author(s):  
Miles Aukland ◽  
Mindaugas Šiaučiulis ◽  
Adam West ◽  
Gregory Perry ◽  
David Procter
Keyword(s):  
Natural Product ◽  
Selective Reduction ◽  
Cross Coupling ◽  
One Pot ◽  
Complex Molecules ◽  
Pummerer Reaction ◽  
Metal Free ◽  
Bond Forming ◽  
Coupling Partner ◽  
Bioactive Natural Product

<p>Aryl–aryl cross-coupling constitutes one of the most widely used procedures for the synthesis of high-value materials, ranging from pharmaceuticals to organic electronics and conducting polymers. The assembly of (hetero)biaryl scaffolds generally requires multiple steps; coupling partners must be functionalized before the key bond-forming event is considered. Thus, the development of selective C–H arylation processes in arenes, that side-step the need for prefunctionalized partners, is crucial for streamlining the construction of these key architectures. Here we report an expedient, one-pot assembly of (hetero)biaryl motifs using photocatalysis and two non-prefunctionalized arene partners. The approach is underpinned by the activation of a C–H bond in an arene coupling partner using the interrupted Pummerer reaction. A unique pairing of the organic photoredox catalyst and the intermediate dibenzothiophenium salts enables highly selective reduction in the presence of sensitive functionalities. The utility of the metal-free, one-pot strategy is exemplified by the synthesis of a bioactive natural product and the modification of complex molecules of societal importance.</p>

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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