An expedient, efficient and solvent-free synthesis of T3P®-mediated amidation of benzhydrols with poorly reactive N-nucleophiles under MW irradiation

Cheruku, Srinivas; Sandhya, Nagarakere C.; Narayana, Yatheesh; Sunilkumar, Makanahalli P.; Kumara, Manikya; Rangappa, Kanchugarakoppal S.; Mantelingu, Kempegowda

doi:10.1039/d1nj04502d

Cited by 4 publications

(1 citation statement)

References 40 publications

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“…Microwave irradiation has been used to improve different organic syntheses because it may couple directly with the reaction molecule and pass thermal conductivity, resulting in a rapid and even temperature rise. Microwave synthesis is a significant advancement in synthetic chemistry [5] An important shift in the way chemical synthesis is accomplished [6] . Traditional heating has long been recognised as inefficient, time‐consuming, and artistically limiting [7] .…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Synthesis and Characterization of Some Aldehyde Derivatives of Imidazo[2,1‐b][1,3,4]thiadiazole: Crystal Structure Insights, In‐Silico and Biological Studies

Sagar,

Kumara,

et al. 2023

ChemistrySelect

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The microwave‐assisted synthesis, crystallographic studies, in‐silico docking and the evaluation of in‐vitro biological activities of 2‐(3,4‐dimethoxy)‐6‐(substituted phenyl)‐ imidazo[2,1‐b][1,3,4]thiadiazole‐5‐carbaldehydes is represented here. Single‐crystal X‐ray diffraction experiments were used to identify the crystal structure of the 6‐(4‐chlorophenyl)‐2‐(3,4‐dimethoxybenzyl)imidazo[2,1‐b][1,3,4]thiadiazole‐5‐carbaldehyde. Using fingerprint plots, Hirshfeld surface analysis was used to confirm the contributions of distinct intermolecular interactions in the development of the crystal packing. Further, density functional theory calculations were employed to calculate the molecule's electronic properties. The chemically active regions on the molecule are identified by analysing the molecular electrostatic potential map. in‐silico studies revealed that the molecules can be effectively used as antibacterial agents by taking the 3q82 receptor with chloramphenicol as a standard. As compared to the chloramphenicol standard, in‐vitro tests showed that molecules 4 a, 4 b, 4 c, and 4 f had a zone of inhibition that ranged from 9 to 11 mm against both Gram‐positive (Bacillus subtilis) and Gram‐negative (Escherichia coli) bacteria. The minimum inhibitory concentration was between 40 to 70 μg/ml. These compounds′ Hydroxyl free radical scavenging activity was between 40 to 85 %. Whereas, DPPH radical scavenging activity was between 40 and 70 %. Percentage hemolysis or cell protective activity of the compounds was ineffective at 20–40 %.

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Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Synthesis and Characterization of Some Aldehyde Derivatives of Imidazo[2,1‐b][1,3,4]thiadiazole: Crystal Structure Insights, In‐Silico and Biological Studies

Sagar,

Kumara,

et al. 2023

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Iron‐Based Deep Eutectic Solvents: Key Players for Amide and Sulfonamide Synthesis and Alcohol Oxidation

Cicco,

Urselli,

Favia

et al. 2024

Eur J Org Chem

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A sustainable protocol has been devised for the oxidation of activated secondary alcohols to their corresponding carbonyl compounds, as well as their utilization as selective mono‐alkylating reagents for both amide and arylsulfonamide derivatives. These reactions proceed smoothly and in good yields (up to 98%) when conducted in Fe‐based deep eutectic solvents (DESs), which serve dual roles as solvents and catalysts. Operating under mild (40 °C) and aerobic conditions, these transformations are completed within a 4 h time frame. A pharmacologically relevant amide derivative, specifically a PMRT1 inhibitor, has also been successfully synthesized on a 3 g‐scale utilizing a reusable FeCl3·6H2O/glycerol Lewis acidic DES.

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The use of microwave radiations and propylphosphonic anhydride (T3P®) for rapid and highly yielding amide bond formation and peptide coupling

Rouge,

Brunel

2024

Tetrahedron

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An expedient, efficient and solvent-free synthesis of T3P®-mediated amidation of benzhydrols with poorly reactive N-nucleophiles under MW irradiation

Abstract: An expedient, efficient, economical, environmentally benign, and solvent-free amidation protocol of benzhydrols with less reactive nitrogen nucleophiles assisted by propylphosphonic anhydride (T3P®) under microwave irradiation has been developed. The methodology...

Cited by 4 publications

References 40 publications

Microwave‐Assisted Synthesis and Characterization of Some Aldehyde Derivatives of Imidazo[2,1‐b][1,3,4]thiadiazole: Crystal Structure Insights, In‐Silico and Biological Studies

Microwave‐Assisted Synthesis and Characterization of Some Aldehyde Derivatives of Imidazo[2,1‐b][1,3,4]thiadiazole: Crystal Structure Insights, In‐Silico and Biological Studies

Iron‐Based Deep Eutectic Solvents: Key Players for Amide and Sulfonamide Synthesis and Alcohol Oxidation

The use of microwave radiations and propylphosphonic anhydride (T3P®) for rapid and highly yielding amide bond formation and peptide coupling

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