Synthesis of Indoline‐Fused 2,5‐Diketopiperazine Scaffolds via Ugi‐4CR in the Basic Mediated Tandem Consecutive Cyclization

This study has developed a method to prepare diastereo‐ and regio‐selective indoline‐fused 2,5‐diketopiperazine scaffolds. The synthetic process involved an Ugi four‐component reaction in which readily available starting materials were used and a metal‐free intramolecular post‐Ugi tandem consecutive...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2021-11, Vol.363 (21), p.4960-4968
Main Authors: Wu, Chih‐Yu, Murugan, Sivan Perumal, Wang, Yu‐Wei, Pan, Hao‐Wei, Sun, Bing‐Jian, Lin, Yu‐Ting, Fatimah, Siti, Chang, Agnes H. H., Chen, Chinpiao, Lee, Gene‐Hsian
Format: Article
Language:English
Subjects:
2,5-Diketopiperazine
Crystal structure
Cyclization
Density functional theory
Indoline-fused 2,5-Diketopiperazine
Multicomponent reactions
Post-Ugi transformation
Scaffolds
Substrates
Ugi-4CR
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:This study has developed a method to prepare diastereo‐ and regio‐selective indoline‐fused 2,5‐diketopiperazine scaffolds. The synthetic process involved an Ugi four‐component reaction in which readily available starting materials were used and a metal‐free intramolecular post‐Ugi tandem consecutive 5‐exo‐trig/6‐exo‐dig cyclization under basic conditions. The plausible mechanism and substrate structures were elucidated by single‐crystal X‐ray diffraction analysis and supported by density functional theory calculations.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202100658