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Access to 3-Amino-[1,2,4]-triazolo Pyridines and Related Heterocycles via Electrochemically Induced Desulfurative Cyclization

Yunfei Hu, Li Chen, Canlin Zou, Jiangtao He, Luanqi Feng, Jia‐Qiang Wu, Wen‐Hua Chen, Jinhui Hu

2022Organic Letters27 citationsDOI

Abstract

An efficient, one-pot approach has been established for synthesizing a wide range of 3-amino-[1,2,4]-triazolo pyridines and related heterocycles from the electrochemically induced desulfurative cyclization of 2-hydrazinopyridines with isothiocyanates. The protocol allows for the formation of C-N bonds under simple conditions without transition metals or external oxidants. The practicability of this strategy is demonstrated by its broad substrate scope, good functional group compatibility, and gram-scale synthesis. The late-stage modification of 3-amino-[1,2,4]-triazolo pyridines enables us to obtain several molecules with potent anticancer activity.

Topics & Concepts

ChemistryCombinatorial chemistryFunctional groupSubstrate (aquarium)MoleculeStereochemistryOrganic chemistryPolymerGeologyOceanographyChemistry and Chemical EngineeringSynthesis and Biological EvaluationSulfur-Based Synthesis Techniques
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