Nucleophilic addition of Grignard to acid chloride in the presence of N-Methyl pyrrolidine

10.1039/sp533 ◽  
2012 ◽  
Author(s):  
Ramesha Ramakrishna
Keyword(s):  
Acid Chloride ◽  
Nucleophilic Addition

A Facile Preparation of α-Aryl Carboxylic Acid via One-Flow Arndt–Eistert Synthesis

2015 ◽  
Vol 68 (11) ◽  
pp. 1657 ◽  
Author(s):  
Shinichiro Fuse ◽  
Yuma Otake ◽  
Yuto Mifune ◽  
Hiroshi Tanaka
Keyword(s):  
Carboxylic Acid ◽  
Acid Chloride ◽  
Nucleophilic Addition ◽  
Wolff Rearrangement ◽  
Facile Preparation ◽  
Nucleophilic Acyl Substitution

An efficient, one-flow Arndt–Eistert synthesis was demonstrated. A sequence of acid chloride formation–nucleophilic acyl substitution–Wolff rearrangement–nucleophilic addition was performed in a microflow system without isolating any intermediates, which included a potentially explosive compound. The microflow system was made from simple, inexpensive, and readily available instruments and tubes. α-Aryl esters 2a and 2b were prepared in yields of 33 and 23 % (three steps) respectively.

ChemInform Abstract: NUCLEOPHILIC ADDITION OF HYDROGEN CHLORIDE TO 1,2-ALKADIENEPHOSPHONIC ACID CHLORIDE

1980 ◽  
Vol 11 (36) ◽  
Author(s):  
T. S. MIKHAILOVA ◽  
V. M. IGNAT'EV ◽  
B. I. IONIN ◽  
A. A. PETROV
Keyword(s):  
Hydrogen Chloride ◽  
Acid Chloride ◽  
Nucleophilic Addition

Eco-Friendly Synthesis of Peptides Using Fmoc-Amino Acid Chlorides as Coupling Agent Under Biphasic Condition

2020 ◽  
Vol 27 ◽  
Author(s):  
Santosh Y. Khatavi ◽  
K. Kantharaju
Keyword(s):  
Amino Acid ◽  
Acid Chloride ◽  
Acid Ester ◽  
Analytical Techniques ◽  
Peptide Bond ◽  
Amino Acid Ester ◽  
Acid Chlorides ◽  
Peptide Bond Formation ◽  
Green Protocol ◽  
Additional Base

Background: Agro-waste derived solvent media act as a greener process for the peptide bond formation using Nα - Fmoc-amino acid chloride and amino acid ester salt with in situ neutralization and coupling under biphasic condition. The Fmoc-amino acid chlorides are prepared by the reported procedure of freshly distilled SOCl2 with dry CH2Cl2. The protocol found many added advantages such as neutralization of amino acid ester salt and not required additional base for the neutralization, and directly coupling take place with Fmoc-amino acid chloride gave final product dipeptide ester in good to excellent yields. The protocol occurs with complete stereo chemical integrity of the configuration of substrates. Here, we revisited Schotten-Baumann condition, instead of using inorganic base. Objective: To develop green protocol for the synthesis of peptide bond using Fmoc-amino acid chloride with amino acid esters salt. Methods: The final product isolated is analyzed in several spectroscopic and analytical techniques such as FT-IR, 1H-, 13CNMR, Mass spectrometry and RP-HPLC to check stereo integrity and purity of the product. Conclusion: The present method developed greener using natural agro-waste (lemon fruit shell ash) derived solvent medium for the reaction and not required chemical entity.

Recent Progress in Chemosensors Using Aldehyde-bearing Fluorophores for the Detection of Specific Analytes and their Bioimaging

2019 ◽  
Vol 26 (21) ◽  
pp. 4003-4028 ◽  
Author(s):  
Fangjun Huo ◽  
Yaqiong Zhang ◽  
Caixia Yin
Keyword(s):  
Biomedical Research ◽  
Nucleophilic Addition ◽  
Recent Progress ◽  
Biological Imaging ◽  
Tissue Imaging ◽  
Fluorescence Probes ◽  
Biological Applications ◽  
Convenient Procedure ◽  
Nucleophilic Mechanism

In recent years, aldehyde-appended fluorescence probes have attracted increasing attention. Fluorescent biological imaging includes many modern applications for cell and tissue imaging in biomedical research. Meanwhile, the nucleophilic mechanism is a very simple and convenient procedure for the preparation of aldehyde-sensing probes. This tutorial review focuses on aldehyde-bearing chemosensors based on nucleophilic addition mechanism with biological applications.

Formation of spiro adduct from N-methyl-N-(2,4,6-trinitrophenyl)glycine anion

1989 ◽  
Vol 54 (2) ◽  
pp. 440-445 ◽  
Author(s):  
Vladimír Macháček ◽  
Alexandr Čegan ◽  
Miloš Sedlák ◽  
Vojeslav Štěrba
Keyword(s):  
Nmr Spectroscopy ◽  
Dimethyl Sulfoxide ◽  
Equilibrium Constant ◽  
Mole Fraction ◽  
Nucleophilic Addition ◽  
Adduct Formation ◽  
First Case ◽  
C Nmr

The intramolecular nucleophilic addition of N-methyl-N-(2,4,6-trinitrophenyl)glycine anion in methanol-dimethyl sulfoxide mixtures produces spiro[(3-methyl-5-oxazolidinone)-2,1'-(2',4',6'-trinitrobenzenide)]. The spiro adduct has been identified by means of 1H and 13C NMR spectroscopy. This is the first case when the formation of a Meisenheimer adduct with carboxylate ion is observed. Logarithm of the equilibrium constant of adduct formation increases linearly with the mole fraction of dimethyl sulfoxide in its mixture with methanol.

Regioselective Functionalization of N-Fused Heteroaromatics via FeCl3-Catalyzed Nucleophilic Addition to Activated N-Heterocycles

Synthesis ◽  
2020 ◽  
Author(s):  
Ikyon Kim ◽  
Sung June Kim ◽  
Sunhee Lee
Keyword(s):  
Aromatic Compounds ◽  
Nucleophilic Addition ◽  
Chemical Space ◽  
Wide Range ◽  
Regioselective Functionalization

AbstractBroadening of nitrogen-fused heteroaromatic chemical space such as indolizine and pyrrolo[1,2-a]pyrazine was achieved via FeCl­3-catalyzed nucleophilic addition of these N-fused aromatic compounds to a wide range of azolinium systems generated in situ, leading to novel N-fused heteroaromatic scaffolds with dearomatized N-heterocyclic substituents regioselectively. Nucleophilic addition of indolizines and pyrrolo[1,2-a]pyrazines mainly occurred at the C1 position of the isoquinoliniums and at the C4 site of the quinoliniums.

scholarly journals PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

2021 ◽  
pp. 174751982098753
Author(s):  
Xiaofang Wu ◽  
Lei Zhou ◽  
Fangshao Li ◽  
Jing Xiao
Keyword(s):  
Acid Chloride ◽  
Bioactive Molecules ◽  
Mechanistic Studies ◽  
One Pot ◽  
Tert Butyl ◽  
Butyl Esters

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

Layer by layer assembled functionalized graphene oxide-based polymer brushes for superlubricity on steel-steel tribocontact

Soft Matter ◽  
2021 ◽  
Author(s):  
Suprakash Samanta ◽  
Rashmi Ranjan Sahoo
Keyword(s):  
Graphene Oxide ◽  
Nucleophilic Addition ◽  
Polymer Brushes ◽  
Addition Reaction ◽  
Layer By Layer ◽  
Functionalized Graphene ◽  
Covalent Functionalization ◽  
Functionalized Graphene Oxide ◽  
Nucleophilic Addition Reaction ◽  
Branched Polyethylenimine

Present study demonstrates a simple and multistep approach for the preparation of covalent functionalization of chemically prepared graphene oxide (GO) by branched polyethylenimine (PEI) through nucleophilic addition reaction to prepare...

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