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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

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Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
7.5K
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

3.4K
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
3.4K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

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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.
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Amines: Introduction01:07

Amines: Introduction

6.3K
Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

5.0K
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...
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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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Novel ynamide structural analogues and their synthetic transformations.

Ting Lu, Richard P Hsung

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    PubMed
    Summary

    Novel ynamide analogues offer new synthetic possibilities. These N-containing alkynes are accessible and reactive, serving as versatile building blocks in organic synthesis.

    Keywords:
    Ynimidesamidinyl-ynamidesdiaminoacetylenesyne-hydrazideyne-iminesyne-sulfoximines

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    Area of Science:

    • Organic Chemistry
    • Synthetic Chemistry

    Background:

    • Recent emergence of novel ynamide structural analogues.
    • Growing interest within the synthetic community.

    Purpose of the Study:

    • To delineate the preparations and reactions of de novo ynamide variants.
    • To demonstrate the accessibility and reactivity of these compounds.

    Main Methods:

    • Synthesis of novel ynamide structural analogues.
    • Investigation of their reactivity in organic transformations.

    Main Results:

    • Successful preparation of various de novo ynamide variants.
    • Demonstration of their accessibility and reactivity.

    Conclusions:

    • Novel ynamides are versatile building blocks in organic synthesis.
    • These N-containing alkynes present unique opportunities for synthetic chemists.