scholarly journals Continuous multistep synthesis of 2-(azidomethyl)oxazoles

2018 ◽  
Vol 14 ◽  
pp. 506-514 ◽  
Author(s):  
Thaís A Rossa ◽  
Nícolas S Suveges ◽  
Marcus M Sá ◽  
David Cantillo ◽  
C Oliver Kappe
Keyword(s):  
Process Integration ◽  
Building Blocks ◽  
Subsequent Treatment ◽  
Flow Process ◽  
Synthetic Strategy ◽  
Multistep Synthesis ◽  
Nucleophilic Displacement ◽  
Displacement Reactions ◽  
Continuous Flow Process ◽  
Vinyl Azides

An efficient three-step protocol was developed to produce 2-(azidomethyl)oxazoles from vinyl azides in a continuous-flow process. The general synthetic strategy involves a thermolysis of vinyl azides to generate azirines, which react with bromoacetyl bromide to provide 2-(bromomethyl)oxazoles. The latter compounds are versatile building blocks for nucleophilic displacement reactions as demonstrated by their subsequent treatment with NaN3 in aqueous medium to give azido oxazoles in good selectivity. Process integration enabled the synthesis of this useful moiety in short overall residence times (7 to 9 min) and in good overall yields.

Application of Nitrogen Heterocyclic Carbenes in Organocatalysis

2020 ◽  
Vol 09 ◽  
Author(s):  
Minita Ojha ◽  
R. K. Bansal
Keyword(s):  
Asymmetric Catalysis ◽  
Building Blocks ◽  
Structural Features ◽  
Heterocyclic Carbenes ◽  
Stetter Reaction ◽  
Metal Pollutants ◽  
Synthetic Strategy ◽  
Wide Range ◽  
Benzoin Condensation ◽  
Nitrogen Heterocyclic

Background: During the last two decades, horizon of research in the field of Nitrogen Heterocyclic Carbenes (NHC) has widened remarkably. NHCs have emerged as ubiquitous species having applications in a broad range of fields, including organocatalysis and organometallic chemistry. The NHC-induced non-asymmetric catalysis has turned out to be a really fruitful area of research in recent years. Methods: By manipulating structural features and selecting appropriate substituent groups, it has been possible to control the kinetic and thermodynamic stability of a wide range of NHCs, which can be tolerant to a variety of functional groups and can be used under mild conditions. NHCs are produced by different methods, such as deprotonation of Nalkylhetrocyclic salt, transmetallation, decarboxylation and electrochemical reduction. Results: The NHCs have been used successfully as catalysts for a wide range of reactions making a large number of building blocks and other useful compounds accessible. Some of these reactions are: benzoin condensation, Stetter reaction, Michael reaction, esterification, activation of esters, activation of isocyanides, polymerization, different cycloaddition reactions, isomerization, etc. The present review includes all these examples published during the last 10 years, i.e. from 2010 till date. Conclusion: The NHCs have emerged as versatile and powerful organocatalysts in synthetic organic chemistry. They provide the synthetic strategy which does not burden the environment with metal pollutants and thus fit in the Green Chemistry.

A Continuous Flow Process for LSN647712 via Double Organometallic Additions to Dimethylcarbamyl Chloride

2021 ◽  
Author(s):  
Hui Li ◽  
Jillian W. Sheeran ◽  
David Kouvchinov ◽  
Andrew M. Clausen ◽  
Ian T. Crouch ◽  
...  
Keyword(s):  
Continuous Flow ◽  
Flow Process ◽  
Continuous Flow Process

Assessing inter- and intramolecular continuous-flow strategies towards methylphenidate (Ritalin) hydrochloride

2017 ◽  
Vol 2 (2) ◽  
pp. 149-158 ◽  
Author(s):  
Romaric Gérardy ◽  
Marc Winter ◽  
Alessandra Vizza ◽  
Jean-Christophe M. Monbaliu
Keyword(s):  
Continuous Flow ◽  
Flow Process ◽  
Continuous Flow Process

Development of a scalable continuous-flow process towards enriched threo-methylphenidate (Ritalin) hydrochloride.

The gas phase reactivity of the dimethylchloronium ion with alkylbenzenes

1981 ◽  
Vol 59 (15) ◽  
pp. 2412-2416 ◽  
Author(s):  
John A. Stone ◽  
Margaret S. Lin ◽  
Jeffrey Varah
Keyword(s):  
High Pressure ◽  
Gas Phase ◽  
Mass Spectrometer ◽  
Aromatic Hydrocarbons ◽  
Relative Rate ◽  
Ion Source ◽  
Nucleophilic Displacement ◽  
Rate Of Reaction ◽  
Displacement Reactions ◽  
Bonded Complexes

The reactivity of the dimethylchloronium ion with a series of aromatic hydrocarbons has been studied in a high pressure mass spectrometer ion source using the technique of reactant ion monitoring. Benzene is unreactive but all others, from toluene to mesitylene, react by CH3+ transfer to yield σ-bonded complexes. The relative rate of reaction increases with increasing exothermicity in line with current theories of nucleophilic displacement reactions.

Efficient Synthetic Strategy to Construct Three-Dimensional 4f−5d Networks Using Neutral Two-Dimensional Layers As Building Blocks

2010 ◽  
Vol 49 (13) ◽  
pp. 5971-5976 ◽  
Author(s):  
Hu Zhou ◽  
Ai-Hua Yuan ◽  
Su-Yan Qian ◽  
You Song ◽  
Guo-Wang Diao
Keyword(s):  
Three Dimensional ◽  
Building Blocks ◽  
Two Dimensional ◽  
Synthetic Strategy
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