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Nomenclature of Aryl and Heterocyclic Amines

Nomenclature of Aryl and Heterocyclic Amines

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.

Preparation of Nitriles

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...

Nitriles to Carboxylic Acids: Hydrolysis

Nitriles to Carboxylic Acids: Hydrolysis

Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.

IR Frequency Region: Alkyne and Nitrile Stretching

IR Frequency Region: Alkyne and Nitrile Stretching

Both alkyne (C≡C) and nitrile (C≡N) functional groups contain triple bonds and show stretching absorptions around the wavenumber range of 2100 to 2300 cm−1 in the diagnostic region of the IR spectra.
Comparing the stretching vibrational frequency of C≡C triple bonds with that of double and single bonds, it is evident that C≡C triple bonds exhibit a higher stretching frequency than C=C double and C–C single bonds. Similarly, the C≡N triple bond...

Nitriles to Ketones: Grignard Reaction

Nitriles to Ketones: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard...

Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids

Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids

Although it is possible to reduce a carboxylic acid to an aldehyde, strong reducing agents, like lithium aluminum hydride (LAH), prohibit a controlled reduction, instead causing the generated aldehyde to instantly over-reduce to a primary alcohol.
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H]...

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Accessing α-Arylated Nitriles via BF

Sachin R Shirsath^1,2, Ganesh H Shinde¹, Aslam C Shaikh¹

¹Division of Organic Chemistry , CSIR-National Chemical Laboratory , Pune 411008 , India.

The Journal of Organic Chemistry

|September 12, 2018

Summary

Researchers developed a new method for synthesizing α-diaryl and α-triaryl nitriles using tert-butyl isocyanide as a cyanide source in a 1,6-conjugate addition reaction. This efficient protocol offers good yields and broad substrate scope for versatile chemical synthesis.

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Conjugate addition reactions are fundamental in organic synthesis.
Developing novel cyanide sources for complex molecule synthesis remains a challenge.

Purpose of the Study:

To report a novel BF3·OEt2 catalyzed 1,6-conjugate addition of tert-butyl isocyanide.
To synthesize α-diaryl and α-triaryl nitriles from para-quinone methides and fuchsones.

Main Methods:

Utilized boron trifluoride etherate (BF3·OEt2) as a catalyst.
Employed tert-butyl isocyanide as a novel cyanide source.
Investigated the reaction with para-quinone methides and fuchsones.

Main Results:

Achieved synthesis of α-diaryl and α-triaryl nitriles with good to excellent yields.
Demonstrated a broad substrate scope for the developed protocol.
Established the first use of tert-butyl isocyanide as a cyanide source in 1,6-conjugate addition.

Conclusions:

The developed protocol provides an efficient route to valuable α-diaryl and α-triaryl nitriles.
The synthesized nitriles can be further functionalized, offering versatility in product development.
This work introduces a significant advancement in the application of isocyanides in conjugate addition reactions.