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Updated: Aug 28, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Microwave-assisted one-pot two-step imine formation-hetero-Diels-Alder-detosylation/aromatization sequence: direct
Gowsia Jan1, Atul Kumar1, Muthu Karuppasamy1
1Department of Chemistry and Chemical Sciences, Central University of Jammu, Rahya-Suchani (Bagla), District-Samba, Jammu-181143, J&K, India. vesridharan@gmail.com.
Abstract:
A microwave-assisted, copper-catalyzed, one-pot, two-step reaction is established to access functionalized [1,6]naphthyridines in high yields (up to 96%) starting from 2-(N-propargylamino)benzaldehydes and arylamines. This rapid and operationally simple sequential reaction allowed the construction of two new heterocyclic rings and three new (2 C-C and 1 C-N) bonds in a single synthetic operation. This reaction tolerated various electron-donating and electron-withdrawing substituents well and delivered the desired products in a shorter reaction time under microwave irradiation. This reaction proceeds through a sequential imine formation, intramolecular [4 + 2] hetero-Diels-Alder reaction, and air oxidation, followed by detosylation-aromatization steps.
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