Urea-based DES as an amine source to access nitrogen-containing heterocycles

[Display omitted] •Urea-based DES acts as an amine source, catalyst and solvent for the synthesis of styryl quinazolinones.•Changing the hydrogen bond acceptor in DES to provide different N-substituted styryl quinazolinones.•Overall reaction performed in the greener pathway.•Synthesized molecule act...

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Bibliographic Details
Published in:Tetrahedron letters 2024-09, Vol.148, p.155224, Article 155224
Main Authors: Suresh, Sundararajan, Nawaz Khan, Fazlur Rahman
Format: Article
Language:English
Subjects:
C–H Functionalization
Deep Eutectic solvent
Greener synthesis
Nitrogen heterocycles
Photophysical properties
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Summary:[Display omitted] •Urea-based DES acts as an amine source, catalyst and solvent for the synthesis of styryl quinazolinones.•Changing the hydrogen bond acceptor in DES to provide different N-substituted styryl quinazolinones.•Overall reaction performed in the greener pathway.•Synthesized molecule acts as a security ink in an acidic medium. Herein, we report a urea-based DES that acts as an amine source in the synthesis of N-substituted styryl quinazolinone from anthranilic acid via N-acylation, cyclization, and subsequent sp3 CH functionalization under a green reaction medium. The salient features of this approach are gram-scale synthesis, mild reaction conditions, and a metal-free methodology. Additionally, post-functionalization and photophysical properties were evaluated.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2024.155224