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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...
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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.
Indirect-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship01:29

Indirect-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship

Indirect-acting cholinergic agonists are agents that interact with the acetylcholinesterase enzyme in the synaptic cleft, preventing the breakdown of acetylcholine into choline and acetate. Consequently, the concentration of acetylcholine in the synaptic cleft increases. These agonists can be classified into reversible and irreversible inhibitors based on their duration of action.
Reversible inhibitors display short to medium durations of action. Short-acting agents include simple alcohols with...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an ā€”N=Nā€” link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
Cholinergic Antagonists: Chemistry and Structure-Activity Relationship01:29

Cholinergic Antagonists: Chemistry and Structure-Activity Relationship

Cholinergic antagonists bind to cholinergic receptors and limit the effects of acetylcholine and other cholinergic agonists. Based on the specific cholinergic receptor affinity, these antagonists are classified as muscarinic or nicotinic. Anticholinergics interrupt parasympathetic innervations while sympathetic innervations remain uninterrupted. Muscarinic antagonists are also called 'muscarinic antagonists', 'antimuscarinics', or 'parasympatholytics'. Nicotinic antagonists are called...
Physical Properties of Amines01:26

Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.

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Related Experiment Video

Updated: Jun 6, 2026

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
09:04

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

Published on: September 9, 2016

Guanidine chemistry.

Tsutomu Ishikawa1

  • 1Graduate School of Pharmaceutical Sciences, Chiba University; Chiba 263ā€“8522, Japan. benti@faculty.chiba-u.jp

Chemical & Pharmaceutical Bulletin
|December 9, 2010
PubMed
Summary
This summary is machine-generated.

Guanidines, strong organobases, show diverse utility in organic synthesis. Modified guanidines enable asymmetric synthesis, while bisguanidines offer potential in water purification and chiral applications.

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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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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Facile Preparation of 4-Substituted Quinazoline Derivatives

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A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
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A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

Published on: September 9, 2016

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

Published on: April 27, 2017

Facile Preparation of 4-Substituted Quinazoline Derivatives
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Facile Preparation of 4-Substituted Quinazoline Derivatives

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Asymmetric Synthesis

Background:

  • Guanidines are potent organobases with largely unexplored catalytic applications.
  • Systematic investigation into guanidine derivatives is crucial for advancing organic synthesis.

Purpose of the Study:

  • To explore the catalytic and synthetic potential of modified guanidines and bisguanidines.
  • To develop novel chiral auxiliaries and synthetic methodologies using guanidine scaffolds.

Main Methods:

  • Design and synthesis of chiral guanidines for asymmetric catalysis.
  • Utilizing guanidinium ylides for aziridine formation and subsequent transformations.
  • Investigating the proton and metal ion complexation of bisguanidines.
  • Exploring asymmetric crystallization of modified bisguanidines.

Main Results:

  • Modified guanidines demonstrated efficacy in both catalytic and stoichiometric asymmetric syntheses.
  • Aziridine-2-carboxylates were synthesized from guanidinium salts and aldehydes, serving as versatile building blocks.
  • Bisguanidines exhibited strong complexation with protons and metal ions, indicating potential for environmental remediation.
  • Asymmetric crystallization of monoalkylated bisguanidines revealed inherent chirality due to planar asymmetry.

Conclusions:

  • Guanidines and their derivatives represent a versatile class of compounds with significant applications in asymmetric synthesis and materials science.
  • The study highlights novel synthetic routes and potential environmental applications for guanidine-based compounds.