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Updated: Jul 8, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthesis of Azonia Aromatic Heterocycles Bearing 6-6-6-5-6 Pentacyclic Core via Intramolecular [4 + 2]-Cycloaddition
Manoj Kumar Saini1, Karmdeo Prajapati1, Ashok K Basak1
1Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221005, India.
Abstract:
Cationic aza-heterocycle-fused compounds have gained wide applications in materials science, biological applications, and synthetic organic chemistry. In this report, synthesis of benzothiazolochromenopyridinium tetrafluoroborates, a novel molecular scaffold, bearing 6-6-6-5-6 pentacyclic core is described that proceeds via (i) piperidine-catalyzed Knoevenagel condensation between 2-propargyloxyarylaldehydes bearing internal alkynes and 2-benzothiazoleacetonitrile, (ii) intramolecular formal [4 + 2]-cycloaddition, and (iii) crucial molecular oxygen-mediated oxidative aromatization reaction sequence in one pot. These quaternary pyridinium salts are obtained at ambient temperature in good to high yields.
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