Related Experiment Video
Updated: Jan 18, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Light-Promoted C(sp3)-H Functionalization: Alkyl Amines as C2 Synthons in Formal [3+2] Cycloaddition with
Mengting Liu1, Wang Yu1, Jing Li2
1College of Chemistry, International Phosphorus Laboratory, Zhengzhou University, Zhengzhou 450001, P. R. China.
Abstract:
The classical 1,3-dipolar cycloaddition reaction predominantly generates five-membered heterocycles through cycloaddition between 1,3-dipoles and unsaturated hydrocarbons, such as alkenes or alkynes. Herein, we report a light-mediated approach that employs saturated amines as alternatives to conventional unsaturated hydrocarbons, enabling their reaction with N-imino(iso)quinolinium ylides to achieve efficient synthesis of pyrazolo-fused (iso)quinoline core structures. This method demonstrates operational simplicity, mild reaction conditions, and excellent functional group compatibility. Mechanistic investigations reveal that the N-imino(iso)quinolinium ylides not only serve as substrates but also function as photosensitizers, facilitating the formation of critical pyrazolo-fused (iso)quinoline structural units through the single-electron oxidation of amines to generate enamine intermediates.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
14:11Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Related Concept Videos
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Acid Halides to Amides: Aminolysis
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Preparation of 1° Amines: Azide Synthesis
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...