Iodine catalyzed one-pot four component synthesis of coumarinyl phosphoramidates via sequential addition of reactants

2020 ◽  
Vol 44 (43) ◽  
pp. 18573-18578
Author(s):  
Mohammed Imrankhan ◽  
Kalegowda Shivashankar
Keyword(s):  
Sodium Azide ◽  
Synthetic Route ◽  
One Pot ◽  
Sequential Addition ◽  
Trialkyl Phosphites

An unprecedented synthetic route for the preparation of a library of novel coumarinyl phosphoramidate derivatives via iodine catalysed one-pot four component reactions of ethyl 4-bromo-3-oxo-alkanoate, sodium azide, trialkyl phosphites, and phenols in ethanol is reported.

scholarly journals An efficient and practical chemo-enzymatic route to (3R,3aR,6R,6aR)-hexahydrofuro[3,2-b]furan-6-amino-3-ol (6-aminoisomannide) from renewable sources

SynOpen ◽  
2021 ◽  
Author(s):  
Valerio Zullo ◽  
Antonella Petri ◽  
Anna Iuliano
Keyword(s):  
Hydroxy Group ◽  
Sodium Azide ◽  
Hydroxyl Group ◽  
Azido Group ◽  
One Pot ◽  
Renewable Sources ◽  
Nucleophilic Displacement ◽  
Trifluoromethanesulfonic Anhydride ◽  
Enzymatic Route

The synthesis of 6-aminoisomannide is easily achieved starting from the renewable, inexpensive and commercially available isosorbide, in 66% overall yield. A biocatalysed highly regioselective acetylation of the 3-endo hydroxyl group of isosorbide was followed by the stereospecific interconversion of the 6-exo hydroxyl group into azido group, through reaction with trifluoromethanesulfonic anhydride followed by nucleophilic displacement of the triflate group by sodium azide. Finally, reduction of the azido group and deacetylation of the 3-hydroxy group were performed one pot by using LiAlH4.

A green synthetic route for the surface-passivation of carbon dots as an effective multifunctional fluorescent sensor for the recognition and detection of toxic metal ions from aqueous solution

2019 ◽  
Vol 11 (4) ◽  
pp. 490-506 ◽  
Author(s):  
K. Radhakrishnan ◽  
P. Panneerselvam ◽  
M. Marieeswaran
Keyword(s):  
Aqueous Solution ◽  
Quantum Dots ◽  
Carbon Dots ◽  
Surface Passivation ◽  
Fluorescent Sensor ◽  
Toxic Metal ◽  
Carbon Quantum Dots ◽  
Synthetic Route ◽  
One Pot ◽  
Hydrothermal Methods

In this work, a green synthetic route was used to create a number of surface passivated fluorescent carbon quantum dots, which are explored as promising sensing probes, via facile one-pot hydrothermal methods.

One-pot synthesis of 1-substituted 1H-1,2,3,4-tetrazoles from 2aminothiazoles using tributylmethylammonium chloride as a catalyst

2017 ◽  
Vol 23 (5) ◽  
Author(s):  
Kerru Nagaraju ◽  
Gummidi Lalitha ◽  
Parvesh Singh ◽  
Chunduri Venkata Rao
Keyword(s):  
Sodium Azide ◽  
Triethyl Orthoformate ◽  
One Pot ◽  
One Pot Synthesis ◽  
Substituted 1

AbstractReaction between substituted thiazolylamine or oxazolylamine, triethyl orthoformate and sodium azide in the presence of tributylmethylammonium chloride in DMSO furnishes 1-substituted 1

scholarly journals Unsymmetrical Difunctionalization of Two Different C–H Bonds in One Pot Under Transition-Metal Catalysis

Synthesis ◽  
2018 ◽  
Vol 51 (01) ◽  
pp. 40-54 ◽  
Author(s):  
Masahito Murai ◽  
Kazuhiko Takai
Keyword(s):  
Transition Metal ◽  
Functional Groups ◽  
Aromatic Compounds ◽  
Transition Metal Catalysis ◽  
One Pot ◽  
Metal Catalysis ◽  
Selective Functionalization ◽  
Sequential Addition ◽  
Target Molecules ◽  
Directing Group

Recent advancements in unsymmetrical difunctionalization based on the substitution of two different C–H bonds in one-pot are described. Due to the difficulty of controlling reactivity and selectivity, multi-functionalization via substitution of several C–H bonds to install different functional groups has been limited until recently, in comparison with well-studied functionalization via sequential addition to unsaturated π-bonds. This difunctionalization protocol provides an efficient and rapid approach to a library of structurally complicated target molecules through the formation of multiple C–X bonds with high atom- and step-economy.1 Introduction2 ortho-Selective Functionalization of Two Different C–H Bonds Relative to the Directing Group2.1 Unsymmetrical Difunctionalization with the Introduction of Similar Functional Groups2.2 Unsymmetrical Difunctionalization with the Introduction of Different Functional Groups2.3 ortho-Selective Unsymmetrical Difunctionalization Promoted by Two Different Directing Groups Appearing During the Progress of the Reaction3 ortho/meta-Selective C–H Bond Difunctionalization Relative to the Directing Group4 Sequential Difunctionalization of Fused Aromatic Compounds and Heterocycles5 Summary and Outlook

scholarly journals Extendable stapling of unprotected peptides by crosslinking two amines with o-phthalaldehyde

2022 ◽  
Vol 13 (1) ◽  
Author(s):  
Bo Li ◽  
Lan Wang ◽  
Xiangxiang Chen ◽  
Xin Chu ◽  
Hong Tang ◽  
...  
Keyword(s):  
Condensation Reaction ◽  
Cysteine Residue ◽  
Amino Groups ◽  
One Pot ◽  
Peptide Substrates ◽  
Peptide Chemistry ◽  
Peptide Modification ◽  
Wide Range ◽  
Sequential Addition ◽  
Aqueous Conditions

AbstractPeptide modification methods that do not rely on the cysteine residue are underdeveloped, and their development could greatly expand the current toolbox for peptide chemistry. During the course of preliminary investigations into the classical ortho-phthalaldehyde (OPA)-amine-thiol condensation reaction, we found that in the absence of thiol, OPA readily condenses with two primary alkyl amines to form a class of underexplored isoindolin-1-imine compounds under mild aqueous conditions. From the intramolecular version of this OPA-2amines reaction, an efficient and selective methodology using mild reaction conditions has been developed for stapling unprotected peptides via crosslinking of two amino groups in both an end-to-side and side-to-side fashion. The stapling method is superfast and broadly applicable for various peptide substrates with the reacting amino groups separated by a wide range of different amino acid units. The macrocyclization reactions of selected substrates are completed within 10 seconds at 5 mM concentration and within 2 minutes at 50 μM concentration. Importantly, the resulting cyclized peptides with an isoindolinimine linkage can be extended in a one-pot sequential addition manner with several different electron-deficient π electrophiles, thereby generating more complex structures.

scholarly journals Synthesis of a Novel Series of Cu(I) Complexes Bearing Alkylated 1,3,5-Triaza-7-phosphaadamantane as Homogeneous and Carbon-Supported Catalysts for the Synthesis of 1- and 2-Substituted-1,2,3-triazoles

Nanomaterials ◽  
2021 ◽  
Vol 11 (10) ◽  
pp. 2702
Author(s):  
Ivy L. Librando ◽  
Abdallah G. Mahmoud ◽  
Sónia A. C. Carabineiro ◽  
M. Fátima C. Guedes da Silva ◽  
Carlos F. G. C. Geraldes ◽  
...  
Keyword(s):  
Aqueous Medium ◽  
Sodium Azide ◽  
Supported Catalysts ◽  
Cycloaddition Reaction ◽  
Water Soluble ◽  
Terminal Alkynes ◽  
One Pot ◽  
Catalytic Systems ◽  
Immobilized Catalyst ◽  
High Yields

The N-alkylation of 1,3,5-triaza-7-phosphaadamantane (PTA) with ortho-, meta- and para-substituted nitrobenzyl bromide under mild conditions afforded three hydrophilic PTA ammonium salts, which were used to obtain a new set of seven water-soluble copper(I) complexes. The new compounds were fully characterized and their catalytic activity was investigated for the low power microwave assisted one-pot azide–alkyne cycloaddition reaction in homogeneous aqueous medium to obtain disubstituted 1,2,3-triazoles. The most active catalysts were immobilized on activated carbon (AC), multi-walled carbon nanotubes (CNT), as well as surface functionalized AC and CNT, with the most efficient support being the CNT treated with nitric acid and NaOH. In the presence of the immobilized catalyst, several 1,4-disubstituted-1,2,3-triazoles were obtained from the reaction of terminal alkynes, organic halides and sodium azide in moderate yields up to 80%. Furthermore, the catalyzed reaction of terminal alkynes, formaldehyde and sodium azide afforded 2-hydroxymethyl-2H-1,2,3-triazoles in high yields up to 99%. The immobilized catalyst can be recovered and recycled through simple workup steps and reused up to five consecutive cycles without a marked loss in activity. The described catalytic systems proceed with a broad substrate scope, under microwave irradiation in aqueous medium and according to “click rules”.

scholarly journals One-Pot, Water-Mediated, H2O2-HCl Catalyzed Synthesis of Benzazepines

2020 ◽  
Vol 32 (5) ◽  
pp. 1165-1168
Author(s):  
Nidhi Singh ◽  
Jaya Pandey
Keyword(s):  
Completion Time ◽  
Synthetic Route ◽  
One Pot ◽  
Conventional Methods ◽  
Time Required ◽  
Nitrogen Bonds

One-pot, multicomponent H2O2-HCl catalyzed system was employed for the synthesis of a series of benzazepine compounds. The implemented procedure oxidized the carbon-nitrogen bonds and produced benzazepines, while integrating diamines and substituted ketone. The advantage of the exercised synthetic route was that the reaction was water mediated and the completion time was quite reduced compared to the time required by conventional methods

Facile Access to 3,4-Disubstituted 2H-Chromenes via Domino [4+2] Annulation

Synthesis ◽  
2020 ◽  
Author(s):  
Sure Siva Prasad ◽  
Dirgha Raj Joshi ◽  
Ikyon Kim
Keyword(s):  
Lewis Acid ◽  
Triethyl Phosphite ◽  
Synthetic Route ◽  
One Pot ◽  
Highly Efficient ◽  
Three Component Coupling

AbstractA highly efficient synthetic route to polysubstituted 2H-chromenes was developed utilizing a domino O-alkylation/intramolecular Horner–Wadsworth–Emmons (HWE) olefination of diarylmethylphosphonates, which were readily accessed via Lewis acid mediated one-pot three-component coupling of aldehydes, phenols, and triethyl phosphite.

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