Synthesis of Azonia Aromatic Heterocycles Bearing 6-6-6-5-6 Pentacyclic Core via Intramolecular [4 + 2]-Cycloaddition and Oxidative Aromatization Reaction Sequence in One Pot

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. © 2023 American Chemical Society