A divergent construction of fused and bridged carbo-/heterocyclic scaffolds via cascade reactions of aryl azomethine imines with vinyl cyclic carbonates

Presented herein is a divergent synthesis of indene-fused pyrazoles and bridged benzodiazepines tethered with a versatile reactive hydroxymethyl group via the cascade reactions of aryl azomethine imines with vinyl cyclic carbonates. Mechanistically, the reactions are initiated by TM-catalysed aryl C...

Full description

Saved in:
Bibliographic Details
Published inORGANIC CHEMISTRY FRONTIERS Vol. 10; no. 4; pp. 1015 - 1021
Main Authors Cai, Xinyuan, Song, Xia, Yang, Xueying, Zhang, Xinying, Fan, Xuesen
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.02.2023
Royal Society of Chemistry
Subjects
Agrochemicals
Aromatic compounds
Benzodiazepines
Carbonates
Cascade chemical reactions
Chemistry
Chemistry, Organic
Cycloaddition
Decarboxylation
Hydrogen bonds
Imines
Indene
Organic chemistry
Physical Sciences
Pyrazoles
Science & Technology
Substrates
MILD
ACTIVATION
C-H FUNCTIONALIZATION
ACCESS
ALLYLATION
Online AccessGet full text

Cover

More Information
Summary:Presented herein is a divergent synthesis of indene-fused pyrazoles and bridged benzodiazepines tethered with a versatile reactive hydroxymethyl group via the cascade reactions of aryl azomethine imines with vinyl cyclic carbonates. Mechanistically, the reactions are initiated by TM-catalysed aryl C(sp(2))-H bond activation/cyclometallation, followed by vinyl coordination/migratory insertion, elimination/decarboxylation and intramolecular [3 + 2] cycloaddition. By using this developed protocol, a number of fused and bridged carbo-/heterocyclic products with pharmaceutical and agrochemical significance are readily obtained from easily obtainable substrates in an efficient and atom-economical manner. Moreover, the usefulness of this method is showcased by gram-scale preparations and diverse transformation of the products.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d2qo01897g