Wool-SO3H and nano-Fe3O4@wool as two green and natural-based renewable catalysts in one-pot isocyanide-based multicomponent reactions

Shaabani, Ahmad; Hezarkhani, Zeinab; Faroghi, Mohammad Tayeb

doi:10.1007/s00706-016-1717-7

Cited by 16 publications

(4 citation statements)

References 37 publications

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“…2,3-Diaminomaleonitrile (DAMN) is considered as one of the versatile precursors for the synthesis of various types of nitrogen containing heterocycles, such as, imidazoles, purines, pyrazines, pyrimidines, oxazoles, diazepines, andtriazepines, and pyrroles. − Shaabani et al developed an efficient one-pot reaction for the synthesis of 4,5,6,7-tetrahydro-1 H -1,4-diazepine-5-carboxamide derivatives 223 and 2,3,4,5-tetrahydro-1 H -1,5-benzodiazepine-2-carboxamide derivatives 222 (Scheme ). − This pseudo-five-component condensation is performed by 2,3-diaminomaleonitriles 221 or aromatic diamines 201 , ketones 106 , isocyanides 5 , and water in the presence of a catalytic amount of p -toluenesulfonic acid in mild conditions at room temperature.…”

Section: Cyclic Imines In Joulliè−ugi Reactionmentioning

confidence: 99%

Cyclic Imines in Ugi and Ugi-Type Reactions

et al. 2020

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Ugi four-component reactions (U-4CRs) are widely recognized as being highly efficient for the synthesis of pseudopeptides. However, the products of these reactions are not so interesting as drug candidates because they are not conformationally restricted enough for a potent interaction with biological targets. One possible way to overcome this problem is to replace amine and oxo components in the U-4CRs with cyclic imines in so-called Joullié−Ugi three-component reactions (JU-3CRs). This approach provides a robust single-step route to peptide moieties connected to N-heterocyclic motifs that are found as core skeletons in many natural products and pharmaceutical compounds. JU-3CRs also provide much better diastereoselectivity than their four-component analogues. We survey here the redesign of many synthetic routes for the efficient preparation of a wide variety of three-, five-, six-, and seven-membered heterocyclic compounds connected to the peptide backbone. Additionally, in the Ugi reactions based on the cyclic imines, α-acidic isocyanides, or azides can be replaced with normal isocyanides or acids, respectively, leading to the synthesis of N-heterocycles attached to oxazoles or tetrazoles, which are of great pharmaceutical significance. This Review includes all research articles related to Ugi reactions based on the cyclic imines to the year 2020 and will be useful to chemists in designing novel synthetic routes for the synthesis of individual and combinatorial libraries of natural products and drug-like compounds.

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Section: Cyclic Imines In Joulliè−ugi Reactionmentioning

confidence: 99%

Cyclic Imines in Ugi and Ugi-Type Reactions

et al. 2020

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“…disclosed the synthesis of (cyanophenylamino)acetamide derivatives 16 with the successful usage of natural wool sulfonic acid (wool‐SO 3 H) or wool‐supported Fe 3 O 4 nanoparticles (nano‐Fe 3 O 4 @wool) as catalyst (Scheme 4). [ 37 ] Both these catalysts were found to be highly efficient; however, Fe 3 O 4 @wool catalyst was the best for this method due to its comparatively easy separation technique.…”

Section: Classificationmentioning

confidence: 99%

Recent advances in the iron‐catalysed multicomponent reactions

Saranya

Aneeja

Neetha

et al. 2020

Applied Organom Chemis

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Iron‐catalysed reactions are widely used in organic synthesis owing to its benefits over other metals. Among the important organic reactions, multicomponent reactions play a significant role due to its greener aspects like high atom economy, minimal amount of by‐product, economic feasibility etc. For the past few years, iron‐catalysed multicomponent reactions have attracted the attention of several chemists which lead to the invention of some fine chemistry. The majority of iron‐catalysed multicomponent reactions results in the synthesis of heterocyclic compounds having biologically active natural products, pharmaceutical etc. These developments in the iron‐catalysed multicomponent reactions are the focus of this review. This is the first review in this topic which covers the literature up to 2020, and it encompasses the different methods for the synthesis of acyclic, carbocyclic and heterocyclic compounds.

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“…Also, design a carrier system that can selectively deliver cytotoxic doses of therapeutic agents to cancer without any cytotoxic effect received significant attention [4,5]. Recently, magnetic nanoparticles have been comprehensively studied and broadly exploited in catalytic processes [6][7][8] and biomedical applications including magnetic resonance imaging (MRI) [9,10], drug delivery [11,12], gene delivery [13], bacterial detection [14,15], and cell separation [16,17], because of their unique properties counting high magnetic sensitivity, good biocompatibility and low toxicity. Magnetic nanoparticles can be coated and functionalized with a wide sort of various small and macro molecules such as organic compounds, metals and poly-…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis and Characterization of L-Aspartic Acid Coated Iron Oxide Magnetic Nanoparticles (IONPs) For Biomedical Applications

et al. 2017

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Natural L-aspartic acid coated iron oxide magnetic nanoparticles (Asp@IONPs) were prepared by a one pot, in-situ and green co-precipitation method in an aqueous medium. Functionalized iron oxide magnetic nanoparticles (IONPs) were characterized by Vibrating Sample Magnetometer (VSM), X-ray diffraction (XRD), differential scanning calorimetry (DSC), Fourier transform infrared spectroscopy (FTIR), Scanning electron microscopy (SEM) and Transmission electron microscopy (TEM) techniques. Cellular toxicity of IONPs was also investigated on HEK-293 cell lines. The results showed that the zeta potential of Asp@IONPs was about -21.1 mV and the average size was 17.80±3.09 nm. Cell toxicity results show that as prepared IONPs are biocompatible. Asp@IONPs show the possibility of using these nanoparticles in the development of in vitro and in vivo biomedical fields due to do not possess a toxic effect, good ζ-potential and related small and narrow size distribution.

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Wool-SO3H and nano-Fe3O4@wool as two green and natural-based renewable catalysts in one-pot isocyanide-based multicomponent reactions

Cited by 16 publications

References 37 publications

Cyclic Imines in Ugi and Ugi-Type Reactions

Cyclic Imines in Ugi and Ugi-Type Reactions

Recent advances in the iron‐catalysed multicomponent reactions

Facile Synthesis and Characterization of L-Aspartic Acid Coated Iron Oxide Magnetic Nanoparticles (IONPs) For Biomedical Applications

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