Heteroatom-Activated Cyclization: A Unified Route to Diverse Six-Membered N-Heterocycles from Homopropargylic Amines
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Updated: May 15, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Zhaoxia Zhong1, Aorou Song1, Xuejie Liu2
1School of Pharmacy and Key Laboratory of Molecular Pharmacology and Drug Evaluation (Ministry of Education), Yantai University, Yantai 264005, China.
Abstract:
We report a unified, metal-free strategy that employs terminal heteroatom (chalcogen or halogen)-substituted homopropargylic amines as key substrates. Their cyclization with heteroallenes (e.g., CO2, CS2, isocyanates) under mild conditions efficiently affords three classes of six-membered N-heterocycles. The protocol is scalable and the products feature a versatile exocyclic vinyl-heteroatom handle for diversification. Mechanistic studies, supported by DFT calculations, highlight the heteroatom's essential function in activating the alkyne for the pivotal 6-exo-dig cyclization.
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