A novel multicomponent reaction between amino acids, aromatic aldehydes and<i>p</i>-toluenesulfonylmethyl isocyanide: an efficient and green one-pot synthesis using nanosilica

Edjlali, Ladan; Vessally, Esmail; Jafari, Zahra; Esrafili, Mehdi D.

doi:10.1080/17518253.2015.1116617

Cited by 5 publications

(5 citation statements)

References 29 publications

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“…Ugi reaction belongs to the class of isocyanide based multicomponent reaction which requires a primary amine, aldehyde or ketone, a carboxylic acid, and an isocyanide . A variety of bisamides, pseudopeptides having suitable biological activity can be derived from the four component Ugi reaction as four different functional groups take part in the reaction . Moreover, the atom economy and efficiency of the reaction is high, and it can be carried out in mild organic solvents and water, which makes it attractive to the pharmaceutical industries for exploiting the reaction for large-scale production of biologically active compounds .…”

Section: Introductionmentioning

confidence: 99%

“… 66 A variety of bisamides, pseudopeptides having suitable biological activity can be derived from the four component Ugi reaction as four different functional groups take part in the reaction. 67 Moreover, the atom economy and efficiency of the reaction is high, and it can be carried out in mild organic solvents and water, which makes it attractive to the pharmaceutical industries for exploiting the reaction for large-scale production of biologically active compounds. 68 Using an Ugi reaction, alginates can be converted to amphiphilic bisamides suitable for pharmaceutical applications especially for hydrophobic drug delivery and sustained drug release ( Figures 8 and 9 ).…”

Section: Introductionmentioning

confidence: 99%

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A Review on Hydrophobically Associated Alginates: Approaches and Applications

Akshaya,

Nathanael

2024

ACS Omega

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Alginates are linear anionic polysaccharides, which are well-known for their biocompatible, nontoxic, and biodegradable nature. The polymer consists of alternating units of β-(1 → 4)-linked D-mannuronic acid (M) and α-(1 → 4)-linked L-guluronic acid (G) that have hydroxyl and carboxyl groups as the main functional groups. As a large number of free carboxyl and hydroxyl groups are present in the polymeric chain, the polymer is predominantly hydrophilic. The food and pharmaceutical industries have been the most extensive utilizers of alginates to produce gelling and thickening agents. However, by imparting hydrophobicity to alginates, the range of applications can be widened. Although there are reviews on alginate and its chemical modifications, reviews focusing on hydrophobically associated alginates have not been presented. The commonly used chemical modifications to incorporate hydrophobicity include esterification, Ugi reaction, reductive amination, and graft copolymerization. The hydrophobically modified alginates play an important role in delivery of hydrophobic drugs and pesticides as the modification increases the affinity toward hydrophobic components and helps in their sustained release. Due to their nontoxic and edible nature, they find use in the food industry as emulsion stabilizer to stabilize oil-in-water emulsions and to improve creaming ability. Further, alginate-based materials such as membranes, aerogels, and films are hydrophobically modified to improve their functionality and applicability to water treatment and food packaging. This Review aims to highlight the important chemical modifications and methods that are done to impart hydrophobicity to alginate, and the applications of hydrophobically modified alginates in different sectors ranging from drug delivery to food packaging are discussed.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Review on Hydrophobically Associated Alginates: Approaches and Applications

Akshaya,

Nathanael

2024

ACS Omega

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“…Numerous research papers are being continuously published in the field of organic synthesis with greater emphasis on the development of novel catalysts, novel reactions and novel synthetic methodologies . Modern synthetic chemists are in a constant pursuit of developing eco‐friendly processes whereby cleaner protocols are being adopted to achieve higher product yields with simple operational steps having higher selectivity in shorter reaction times.…”

Section: Introductionmentioning

confidence: 99%

l‐Glutamine Supported on Core–Shell Silica Iron Oxide Nanoparticles: A Highly Efficient Organocatalyst for Synthesis of Spirooxoindoles

et al. 2019

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A novel, eco‐friendly super paramagnetic organo‐nano catalyst was fabricated by encapsulating ferrite@silica (Fe3O4@SiO2) nanoparticles with l‐Glutamine. The prepared catalyst was characterized by various analytical techniques viz., fourier transform infrared spectroscopy (FT‐IR), thermogravimetric analysis (TGA), transmission electron microscopy (TEM), Scanning electron microscopy (SEM), Energy Dispersive X‐ray analysis (EDX), powder X‐ray diffraction technique (XRD), vibrating sample magnetometer spectroscopy (VSM), Inductively coupled plasma optical emission spectroscopy (ICP‐OES) and its catalytic activity was investigated for the synthesis of spirooxindole derivatives. Utilizing the ferromagnetic nature of Fe3O4 nanoparticles, the prepared catalyst could be easily retrieved from the reaction mixture after completion of the reaction by using an external magnet. The catalyst was reused up to six runs with remarkable catalytic activity. The main advantages of this synthetic approach lie in its operational simplicity, cost effectiveness, higher yields, easy catalyst recyclability and reusability, eco‐friendly procedures and shorter reaction times. Also, the antimicrobial assay of the synthesized spirooxoindoles was evaluated against three bacterial isolates and one fungal isolate, and the results showed profound antimicrobial activities.

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“…There are many examples of isonitriles in multicomponent reactions for forming original biologically-active compounds [1,2]. They are widely used in green chemistry [3,4,5] and in the synthesis of tetrazoles [6,7,8,9,10,11]. Substituted or heterocyclic annulated tetrazoles have an extensive range of biological activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1-(para-methoxyphenyl)tetrazolyl-Substituted 1,2,3,4-Tetrahydroisoquinolines and Their Transformations Involving Activated Alkynes

et al. 2018

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1-(p-Methoxyphenyl)tetrazolyl-substituted 6,7-dimethoxy(6,7-methylenedioxy)-1,2,3,4-tetrahydroisoquinolines formed tetrazolyl-substituted azocines in high yields by using activated alkynes. Unsubstituted at 6,7,8-aromatic fragment 1-tetrazolylisoquinoline interacted in several pathways forming tetrazolyl-substituted azocines, 1-tetrazolyl-1-R-vinylisoquinolines and 3-azaspiro[5.5]undeca-1,7,9-triene.

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A novel multicomponent reaction between amino acids, aromatic aldehydes andp-toluenesulfonylmethyl isocyanide: an efficient and green one-pot synthesis using nanosilica

Cited by 5 publications

References 29 publications

A Review on Hydrophobically Associated Alginates: Approaches and Applications

A Review on Hydrophobically Associated Alginates: Approaches and Applications

l‐Glutamine Supported on Core–Shell Silica Iron Oxide Nanoparticles: A Highly Efficient Organocatalyst for Synthesis of Spirooxoindoles

Synthesis of 1-(para-methoxyphenyl)tetrazolyl-Substituted 1,2,3,4-Tetrahydroisoquinolines and Their Transformations Involving Activated Alkynes

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