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Updated: Jan 11, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Base-Promoted Azinium-N-imines and Thioamide Dimeric Annulation for the Tunable Synthesis of 1,2,4-Triazole and
Hao Yang1, Meili Zou1, Weiran Yang1
1School of Chemical and Chemical Engineering, Nanchang University, 999 XueFu Road, Nanchang 330031, China.
Abstract:
A base-promoted cycloaddition of azinium-N-imines with thioamides or indolin-2-thiones has been developed for the efficient construction of 1,2,4-triazole and polycyclic indolylhydroquinoline frameworks. This protocol features broad functional group tolerance, scalability, and significantly reduced reaction times. Notably, heteroaromatic N-imines derived from isoquinolinium and quinolinium salts serve as suitable substrates, delivering [1,2,4]triazolo[5,1-a]isoquinoline and [1,2,4]triazolo[1,5-a]quinoline derivatives, respectively, under mild reaction conditions. Furthermore, indole-annulated pentacyclic indolylhydroquinolines can also be accessed by the [3+3] annulation of N-imine quinolinium with indolin-2-thiones. These strategies provide a practical and modular entry to nitrogen- and sulfur-containing polycyclic scaffolds, structurally related to alkaloid natural products.
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