Affiliation:
1. College of Pharmacy Seoul National University 1 Gwanak-ro, Gwanak-gu Seoul 08826 Republic of Korea
Abstract
AbstractAn efficient and facile synthesis of highly substituted pyridinium salts through the annulation of enamines with alkynes is reported herein. A Ag2CO3/HNTf2 synergistically acting catalyst system was developed and used in a condensation reaction between carbonyl substrates and propargylamine to afford structurally diverse pyridinium salts. A mechanistic investigation shows that this one‐pot transformation proceeded via selective 6‐endo‐dig cyclization of the in situ generated propargylenamine and protonolysis of the resulting vinyl–silver intermediate. The reaction conditions are mild, and the substrate scope is broad. During the cyclization, an unusual inversion of the normal reactivity of α,β‐unsaturated carbonyl systems was observed.
Funder
National Research Foundation of Korea
Subject
General Chemistry,Catalysis,Organic Chemistry
Cited by
2 articles.
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