Single Step Upgradation of Isatin to Bioactive Fused Heterocycles via Ring Expansion Reactions

Isatin, also known as indoline‐2,3‐dione, is a fused, N‐heterocyclic aromatic compound first isolated and purified in 1841. Since then, isatin and its derivatives emerged as a hot research topic for the scientific community. The number of research publications on isatin justifies their popularity. R...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2024-01, Vol.27 (4), p.n/a
Main Authors: Chandramani, Raksha, Nair, Ajil R., Sreekumar, Anjana, Aerathupalathu Janardhanan, Jayakrishnan, Sivan, Akhil
Format: Article
Language:English
Subjects:
acridines
Aromatic compounds
Cascade chemical reactions
cycloaddition
Diketones
Heterocyclic compounds
isatin
Multidisciplinary research
Organic chemistry
Organic compounds
quinolines
ring-expansion
spiro compounds
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:Isatin, also known as indoline‐2,3‐dione, is a fused, N‐heterocyclic aromatic compound first isolated and purified in 1841. Since then, isatin and its derivatives emerged as a hot research topic for the scientific community. The number of research publications on isatin justifies their popularity. Researchers explored isatins and their derivatives as potential candidates in multidisciplinary research areas, including medicinal chemistry, synthetic organic chemistry, and polymer science. Synthetic chemists’ perspective of tailoring isatin and its family members led to more efficient synthesis strategies in which ring‐opening reactions of isatins were particularly significant due to the product's importance. Our investigation aims to group the different types of cascade ring expansion reactions of isatin to synthesise fused heterocyclic compounds such as derivatives of quinolines, quinazolinones, acridines, acridones, and few spiro heterocyclic compounds, all of which highlight an inevitable role in the field of medicinal chemistry. The graphical shown here describes the ring expansion reactions of isatin. The 5‐membered ring of isatin is cleaved in different ways to afford a wide variety of heterocyclic organic compounds such as quinolines, spirocyclic derivatives of quinolines, quinazolinones, acridinones and acridines.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202301000