Related Experiment Video
Updated: May 6, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Modular access to N-substituted cis-3,5-diaminopiperidines
Aurélie Blond1, Paul Dockerty, Raquel Álvarez
1Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques, Faculté des Sciences Fondamentales et Biomédicales, UMR8601, CNRS-Paris Descartes University , 45 rue des Saints Pères, 75006 Paris, France.
Researchers developed a new synthetic route to create N-substituted cis-3,5-diaminopiperidines. This method offers a simple and versatile way to access diverse, RNA-friendly molecular fragments.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
Background:
- Piperidines are crucial scaffolds in medicinal chemistry.
- Access to diverse N-substituted piperidines is essential for drug discovery.
- Current synthetic methods may lack generality or efficiency.
Purpose of the Study:
- To develop a novel and efficient synthetic route for N-substituted cis-3,5-diaminopiperidines.
- To provide a general method for accessing diverse RNA-friendly fragments.
- To establish a straightforward preparation from readily available starting materials.
Main Methods:
- A three-step sequence involving oxidative cleavage, reductive amination, and hydrogenolysis.
- Utilizing a readily available bicyclic hydrazine as the starting material.
- Exploring variations for N-substitution to achieve chemical diversity.
Main Results:
- Successful preparation of N-substituted cis-3,5-diaminopiperidines.
- Demonstrated simplicity and generality of the synthetic route.
- Generated a library of RNA-friendly fragments with good chemical diversity.
Conclusions:
- The developed synthetic strategy provides efficient access to valuable N-substituted cis-3,5-diaminopiperidines.
- This method is suitable for generating diverse fragments for medicinal chemistry applications.
- The route offers a practical approach for synthesizing RNA-friendly compounds.
More Related Videos
11:45Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Disubstituted Cyclohexanes: cis-trans Isomerism
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
Diazonium Group Substitution: –OH and –H
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Basicity of Heterocyclic Aromatic Amines