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Updated: Jul 26, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Cu(OTf)2 Enhanced Intramolecular Nucleophilic N-Arylation of 2-Amino-3-arylquinolines
Anwesha Bhattacharya1, Nayanthara Ramesh Babu1, Debashruti Bandyopadhyay1
1School of Chemical Sciences, National Institute of Science Education and Research (NISER) Bhubaneswar, an OCC of Homi Bhabha National Institute, Khurda - 752050, Odisha, India.
Abstract:
In the presence of Cu(OTf)2 (5 mol %) and KOBu, a synergistic effect of the N-arylation process on 2-amino-3-arylquinolines is observed. Within 4 h, this method provides a wide variety of norneocryptolepine analogues with good to excellent yields. Overall, a double heteroannulation strategy for the synthesis of indoloquinoline alkaloids from nonheterocyclic precursors is demonstrated. Mechanistic investigations establish that the reaction proceeds via the SNAr pathway. Despite moderate yields, the one-pot, two-step double heteroannulation illustrates that this procedure is highly atom-efficient. Neocryptolepine, a natural product, is also synthesized from indoloquinoline. A brief study of the photophysical properties of selected norneocryptolepine analogues is also discussed.
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