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Synthesis 2024; 56(20): 3131-3141
DOI: 10.1055/a-2368-8500
DOI: 10.1055/a-2368-8500
feature
Lewis Acid Mediated Synthesis of 4-Aminoquinoline Derivatives from 2-Aminobenzonitriles and Activated Alkynes via Aza-Michael and Annulation Reactions
The authors are grateful to the Science and Engineering Research Board (SERB), New Delhi (Grant No. CRG/2022/001028) for financial support.
Abstract
An efficient methodology for the synthesis of highly diverse 4-aminoquinoline derivatives from activated alkynes and 2-aminobenzonitriles mediated by Lewis acid is described. The reaction proceeds via sequential aza-Michael addition/intramolecular annulation to afford highly substituted 4-aminoquinolines in good yields. The reaction is operationally simple and has high atom-economy with broad substrate scope. The post synthetic application of the reaction provides 4H-benzo[de][1,6]naphthyridines.
Key words
N-heterocycles - 4-aminoquinoline - 2-aminobenzonitrile - propynoate - ynone - aza-Michael - benzannulationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2368-8500.
- Supporting Information
Publication History
Received: 11 June 2024
Accepted after revision: 17 July 2024
Accepted Manuscript online:
18 July 2024
Article published online:
08 August 2024
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