Related Experiment Video
Updated: Aug 23, 2025
10:14
Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
12.6K
Atom Economical Multi-Substituted Pyrrole Synthesis from Aziridine
Lingamurthy Macha1, Ranjith Jala1, Sang-Yun Na1
1Department of Chemistry, Hankuk University of Foreign Studies, Yongin 17035, Korea.
Molecules (Basel, Switzerland)
|October 27, 2022
Summary
A novel synthesis of multi-substituted pyrroles is achieved through regioselective aziridine ring-opening and cyclization. This atom-economical method efficiently produces diverse pyrrole structures, including natural products.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Pyrroles are crucial heterocyclic compounds found in numerous natural products and pharmaceuticals.
- Efficient and versatile synthetic routes to multi-substituted pyrroles are highly sought after in organic synthesis.
Purpose of the Study:
- To develop a novel, atom-economical method for synthesizing multi-substituted pyrroles.
- To demonstrate the applicability of this new protocol to the synthesis of complex pyrrole derivatives and natural products.
Main Methods:
- Regiospecific aziridine ring-opening reactions.
- Intramolecular cyclization facilitated by Lewis or protic acids.
- Synthesis of pyrroles incorporating a carbonyl group at the gamma-position.
Main Results:
- Successful synthesis of various multi-substituted pyrroles.
- High atom economy, with water as the only byproduct.
- Demonstrated utility in synthesizing pyrrole-containing natural products.
Conclusions:
- A new, efficient, and atom-economical protocol for pyrrole synthesis has been established.
- The method offers a versatile approach for accessing diverse pyrrole scaffolds.
- This protocol holds potential for the synthesis of complex molecules and natural products.
Related Concept Videos
01:22Preparation of 1° Amines: Azide Synthesis
4.1K
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...
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...
4.1K
01:20Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
2.0K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.0K
01:14Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
2.2K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.2K
01:25Basicity of Heterocyclic Aromatic Amines
6.2K
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).
6.2K
01:07Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
3.3K
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.
3.3K
01:11Aryldiazonium Salts to Azo Dyes: Diazo Coupling
3.1K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— 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...
3.1K