Related Experiment Video
Updated: Jan 3, 2026
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Photoinduced and N-bromosuccinimide-mediated cyclization of 2-azido-N-phenylacetamides
Zhan-Shan Li1, Wei-Xia Wang, Ji-Dong Yang
1State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou 730000, PR China.
Abstract:
An efficient synthesis of quinoxalin-2(1H)-ones or spiro[cyclohexene-1,2'-imidazol]-4'-ones has been achieved in moderate to high yields by the visible light-induced and N-bromosuccinimide-mediated cyclization reaction of 2-azido-N-phenylacetamides at ambient temperature. Both the regioselectivity and the speed of cyclization are affected by the substituents attached to the phenyl ring. For example, quinoxalin-2-ones are produced as the main products when the substrates bear electron-withdrawing groups at the para-position of the phenyl ring; in contrast, spiro[cyclohexene-1,2'-imidazol]-4'-ones are obtained as the main products when the substrates bear electron-donating groups at the para-position.
More Related Videos
11:45Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Related Concept Videos
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Nucleophilic Aromatic Substitution: Elimination–Addition
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions