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

Manpreet Singh; Vaishali Vaishali; Deepika Deepika; Jyoti Jyoti; Shubham Sharma; Naveen Banyal; Prashant Kumar; Bharti Budhalakoti; Chandi C. Malakar; Virender Singh

doi:10.1055/s-0041-1738447

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(20): 3329-3341
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

Authors

Manpreet Singh

^aDepartment of Chemistry, Dr B R Ambedkar National Institute of Technology (NIT) Jalandhar, 144008, Punjab, India

^bDepartment of Chemistry, Baba Farid College Bathinda, 151001, Punjab, India
Vaishali Vaishali

^aDepartment of Chemistry, Dr B R Ambedkar National Institute of Technology (NIT) Jalandhar, 144008, Punjab, India
Deepika Deepika

^aDepartment of Chemistry, Dr B R Ambedkar National Institute of Technology (NIT) Jalandhar, 144008, Punjab, India
Jyoti Jyoti

^cDepartment of Chemistry, Central University of Punjab, Bathinda, 151401, Punjab, India
Shubham Sharma

^dGBPIET, Pauri Garhwal, Uttarakhand, India
Naveen Banyal

^aDepartment of Chemistry, Dr B R Ambedkar National Institute of Technology (NIT) Jalandhar, 144008, Punjab, India

^cDepartment of Chemistry, Central University of Punjab, Bathinda, 151401, Punjab, India
Prashant Kumar

^aDepartment of Chemistry, Dr B R Ambedkar National Institute of Technology (NIT) Jalandhar, 144008, Punjab, India
Bharti Budhalakoti

^aDepartment of Chemistry, Dr B R Ambedkar National Institute of Technology (NIT) Jalandhar, 144008, Punjab, India
Chandi C. Malakar

^eDepartment of Chemistry, National Institute of Technology (NIT) Manipur Imphal, 795004, Manipur, India
Virender Singh∗

^aDepartment of Chemistry, Dr B R Ambedkar National Institute of Technology (NIT) Jalandhar, 144008, Punjab, India

^cDepartment of Chemistry, Central University of Punjab, Bathinda, 151401, Punjab, India

Abstract

Alle Artikel dieser Rubrik

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 (Φ_F up to 85%) were exhibited by these fluorophores.

Key words

Kumujian C - β-carboline N-fused imidazoles - metal-free synthesis - fluorescent probe - imidazopyridoindole

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