Solvent free, N,N′-carbonyldiimidazole (CDI) mediated amidation

Verma, Sanjeev K.; Ghorpade, Ramarao; Pratap, Ajay; Kaushik, M. P.

doi:10.1016/j.tetlet.2012.01.125

Cited by 45 publications

(39 citation statements)

References 25 publications

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“…We chose 4-(dimethylamino)benzoic acid as shown in Figure 3. Selection of N(CH 3 ) 2 substituent on aromatic ring was based upon the fact that we needed an electron For esterification, COOH of 4-(dimethylamino)benzoic acid was reacted with 1, 1'-carbonyldimidazole 12,13 that incorporated imidazole leaving group in the carboxylic acid group to form B. A was then added to the reaction media along with N(CH 3 ) 3 base to obtain the product C. Obtained spectral data matched up completely with that reported in literature 14 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Novel 1,2-Diol Containing Azo Dyes for Polymeric Substrates

Sheikh

Kazmi

2017

J. Chil. Chem. Soc.

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Two novel 1,2-diol containing azo dyes have been synthesized for application on polymeric textile substrates. We used multistep synthesis scheme which involved selectively bonding azo chromophore with glycerol moiety such that only one alcohol out of the three gets bonded to the chromophore while rest two remain unchanged. The 1,2-diol moiety, common in both dyes, is responsible for forming hydrogen bonds with polar sites on a polymeric substrate. The molecular structure of the final molecule and synthesized intermediates were elucidated by UV/Vis, FT-IR, MS (EI, ESI, and CI) and 1 H-NMR spectroscopic techniques. Dyes were applied to polyester and nylon 66 fabrics as disperse dyes by exhaust dyeing method and furnished good to excellent fastness properties on both of them.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Novel 1,2-Diol Containing Azo Dyes for Polymeric Substrates

Sheikh

Kazmi

2017

J. Chil. Chem. Soc.

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“…The esterification was carried out by CDI which incorporated the imidazole as leaving group in place of basic group -OH. Being an aromatic ring, the imidazole anion is highly stable (closed bonding shell and resonance) (Verma et al, 2012), hence elimination step of acyl addition elimination reaction becomes energetically facile. Acyl addition elimination is facilitated by the same scheme of the replacement of the leaving group usually by reaction of the acid with an inorganic acid such as SOCl2, oxalyl chloride, PCl3 and PCl5 (Roy et al 2016).…”

Section: Discussionmentioning

confidence: 99%

New bioactive triaryl triglyceride esters: Synthesis, characterization and biological activities

Arshad

Sheikh

Kazmi

et al. 2018

Bangladesh J Pharmacol

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Four new bioactive aryl triester derivatives of glycerol and benzoic acids were synthesized. The synthetic compounds were studied for their antimicrobial and urease inhibition activities. Esterification was carried out by using carbonyldiimidazole to enhance the acyl elimination addition reaction with benzoic acid derivatives. The structure of triglycerides were studied by EI-MS, 1H, 13C-NMR, FT-IR and elemental analysis. All synthetic compounds showed urease inhibition activity with highest value of IC50 value 22.4 ± 0.45 μM which is nearest to standard thiourea IC50 value (21.6 ± 0.12 μM). Except compound (3d), all other compounds exhibited antimicrobial activity against Streptococcus pneumoniae, Staphylococcus epidermidis, Bacillus pumilus, Escherichia coli, Pseudomonas aeruginosa and Candida albican.Video Clip of Methodology:7 min 59 sec <a href="https://youtube.com/v/PvGTYUxO7-4">Full Screen</a> <a href="https://youtube.com/watch?v=PvGTYUxO7-4">Alternate</a>

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“…as a base using two different solvents, namely, dichloromethane and toluene by following a literature protocol. 46 Finally, the reaction conditions were successfully optimized with acid (1 eq. ), CDI (1.2 eq.)…”

Section: Chemistrymentioning

confidence: 99%

Microwave-assisted synthesis, biological evaluation and molecular docking studies of new coumarin-based 1,2,3-triazoles

et al. 2020

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Coumarin-based 1,4-disubstituted 1,2,3-triazole derivatives were synthesized using a highly efficient, ecofriendly protocol via a copper(I)-catalyzed click reaction between various substituted arylazides and terminal alkynes. The synthetic route was easy to access and gave excellent yields under microwave irradiation conditions compared to the conventional heating route. The structures of all the compounds were characterized by IR, 1 H NMR, 13 C NMR spectroscopy and mass spectrometry. All the synthesized compounds were screened for their in vitro antimicrobial, antioxidant and anti-inflammatory activities; among all compounds, 8a, 8j, 8k and 8l exhibited better results with respect to standard drugs.Furthermore, molecular docking studies have been carried out with PDB IDs 2VCX (anti-inflammatory), 3VXI (antioxidant), 4GEE (antimicrobial) and 2XFH (antifungal) using the Glide module of the Schrödinger suite. The final compounds 8d, 8e, 8h, and 8k showed the highest hydrogen bond interactions with His-88 and Val-191 proteins and with water in all the proteins.

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Solvent free, N,N′-carbonyldiimidazole (CDI) mediated amidation

Cited by 45 publications

References 25 publications

Synthesis of Novel 1,2-Diol Containing Azo Dyes for Polymeric Substrates

Synthesis of Novel 1,2-Diol Containing Azo Dyes for Polymeric Substrates

New bioactive triaryl triglyceride esters: Synthesis, characterization and biological activities

Microwave-assisted synthesis, biological evaluation and molecular docking studies of new coumarin-based 1,2,3-triazoles

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