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Synthesis 2023; 55(20): 3329-3341
DOI: 10.1055/s-0041-1738447
DOI: 10.1055/s-0041-1738447
paper
Transition-Metal-Free Cascade C–N Bond Formation: An Effective Strategy for the Synthesis of β-Carboline N-Fused Imidazolium Acetates and Estimation of their Light-Emitting Properties
MS, SK, NB, and VS gratefully acknowledge the Council of Scientific and Industrial Research (CSIR), New Delhi, India, for Senior Research Fellowships (SRF) and a research grant [(02)0356/19/EMR-II]. Deepika gratefully acknowledges Dr B R Ambedkar National Institute of Technology (NIT) Jalandhar for a research fellowship. The financial support from the Science and Engineering Research Board, Department of Science and Technology (SERB-DST), New Delhi (EMR/2017/000155 and CRG/2021/007938) is gratefully acknowledged for funding this work. The characterization facility provided by Central Instrumentation Lab and Research Seed Money (CUPB/20-21/443) by the Central University of Punjab, Bathinda is also gratefully acknowledged.
Abstract
A simple, efficient, and practical metal-free protocol has been devised to synthesize imidazopyrido[3,4-b]indole-based fluorophores decorated with carbazole/β-carboline/pyridine scaffolds via three consecutive C–N bond formations in a single operation. A wide range of aromatic amines (2-aminopyridines, 3-aminocarbazole, and anilines) were successfully applied to synthesize the complex imidazolium ions. The significant features of this strategy include high efficiency, mild and environmentally benign reaction conditions, no chromatographic purification, and broad substrate scope with excellent yields of the isolated products. Moreover, excellent photophysical properties (ΦF up to 85%) were exhibited by these fluorophores.
Key words
Kumujian C - β-carboline N-fused imidazoles - metal-free synthesis - fluorescent probe - imidazopyridoindoleSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1738447.
- Supporting Information
Publication History
Received: 13 October 2022
Accepted after revision: 07 June 2023
Article published online:
08 August 2023
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