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Related Concept Videos

Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.7K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.7K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.5K
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...
3.5K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

3.9K
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...
3.9K
Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

2.8K
Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
2.8K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

2.6K
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
2.6K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

5.8K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
5.8K

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Related Experiment Video

Updated: Jun 14, 2025

Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups
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Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups

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Dechlorinative Pyrazinylation of Glycine Derivatives.

Peiqin Zhang1, Delin Guan1, Youwan Ye1

  • 1Gansu International Scientific and Technological Cooperation Base of Water-Retention Chemical Functional Materials, Key Laboratory of Eco-Environment-Related Polymer Materials of Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, China.

Organic Letters
|May 29, 2025
PubMed
Summary

This study introduces a new method for synthesizing alpha-pyrazinyl glycine derivatives using visible light. This efficient process creates compounds with significant potential for drug discovery and pharmaceutical applications.

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

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Last Updated: Jun 14, 2025

Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Drug Discovery

Background:

  • Amino acids and pyrazines are vital components in the development of new drugs.
  • Efficient synthesis of novel chemical entities is crucial for advancing pharmaceutical research.

Purpose of the Study:

  • To develop a visible-light-driven method for the alpha-C(sp3)-H pyrazinylation of glycine derivatives.
  • To enable the efficient synthesis of alpha-pyrazinyl glycine derivatives.

Main Methods:

  • Utilized a visible-light photocatalysis approach.
  • Employed a redox-neutral reaction mechanism.
  • Reacted glycine derivatives with chloropyrazines.

Main Results:

  • Successfully synthesized alpha-pyrazinyl glycine derivatives.
  • Demonstrated an efficient and novel synthetic route.
  • Highlighted the potential biological and pharmaceutical value of the synthesized compounds.

Conclusions:

  • The presented method offers a valuable tool for accessing alpha-pyrazinyl glycine derivatives.
  • This approach facilitates the creation of compounds with potential applications in drug design.
  • Visible-light photocatalysis provides an efficient pathway for pyrazinylation reactions.