Lewis Acid Mediated Synthesis of 4-Aminoquinoline Derivatives from 2-Aminobenzonitriles and Activated Alkynes via Aza-Michael and Annulation Reactions

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 - benzannulation

Publikationsverlauf

Eingereicht: 11. Juni 2024

Angenommen nach Revision: 17. Juli 2024

Accepted Manuscript online:
18. Juli 2024

Artikel online veröffentlicht:
08. August 2024

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