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Updated: Jun 23, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Harnessing the benzyne insertion consequence to enable π-extended pyrido-acridine and quinazolino-phenanthridine
Swarnali Ghosh1, Dwaipayan Das1, Rahul Dev Mandal1
1Department of Chemistry, University of Calcutta, 92, A. P. C. Road, Kolkata-700009, India. ardchem@caluniv.ac.in.
Abstract:
Distinct protocols have been devised for the preparation of hybrid heterocyclic scaffolds like π-extended pyrido-acridines and quinazolino-phenanthridines duly materialized through Rh(III)- and Pd(II)-mediated catalytic courses commencing from acridine and quinazolimine scaffolds. Interestingly, the parent compounds (acridines and quinazolimines) are actualized from 2-aminobenzonitrile and anthranilic acid, where 2-aminobenzonitrile acts as the 1,4-dipolarophilic species and anthranilic acid as the benzyne precursor. The molecular assembly of acridine suggests the participation of two benzyne units. In addition, the structural motif of the quinazolimine ring features one benzyne unit. Further, indolizine ring containing the enaminonitrile skeleton upon exposure to benzyne forms an indolizine fused quinoline ring, decorated with three benzyne units.
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