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Related Concept Videos

Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
Preparation of Nitriles01:12

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

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Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

[The preparative method for 2-fluoroadenosine synthesis].

V B Berzin, E V Dorofeeva, V N Leonov

    Bioorganicheskaia Khimiia
    |June 20, 2009
    PubMed
    Summary
    This summary is machine-generated.

    A new method synthesizes 2-fluoroadenosine from guanosine. This efficient process involves key intermediates and the Schiemann reaction, yielding 74% of the target compound.

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    Area of Science:

    • Organic Synthesis
    • Medicinal Chemistry
    • Nucleoside Chemistry

    Context:

    • Developing novel synthetic routes for modified nucleosides is crucial for drug discovery.
    • Guanosine is a readily available starting material for purine analog synthesis.
    • Fluorinated nucleosides exhibit unique biological properties and therapeutic potential.

    Purpose:

    • To establish a scalable and efficient preparative method for synthesizing 2-fluoroadenosine.
    • To optimize reaction conditions for key steps, including the Schiemann reaction.
    • To characterize intermediates and the final product using spectroscopic techniques.

    Summary:

    • A synthetic route to 2-fluoroadenosine from guanosine was developed.
    • Key steps include the formation of a tetrazolopurine intermediate and its conversion via the Schiemann reaction.
    • Optimized conditions yielded 6-azido-2-fluoro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine at 80% and 2-fluoroadenosine at 74% total yield.

    Impact:

    • Provides a reliable method for producing 2-fluoroadenosine, a valuable compound in medicinal chemistry.
    • Facilitates further research into the biological activities and applications of fluorinated nucleosides.
    • Demonstrates the utility of the Schiemann reaction in synthesizing purine derivatives.