Abstract
An intramolecular transition-metal-free base-mediated hydroamination of propargylamine with isothiocyanates has been achieved. This atom-economical, regioselective intramolecular 5-exo-dig cycloisomerization was utilized for the one-pot synthesis of diversely substituted imidazole-2-thione and spiro-cyclic imidazolidine-2-thione. The reaction goes to completion at room temperature via propargylthiourea and 65-97% isolated yields were obtained.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Catalysis
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Cyclization
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Ethylenethiourea / chemistry*
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Gold / chemistry*
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Imidazoles / chemical synthesis*
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Imidazoles / chemistry
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Molecular Structure
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Pargyline / analogs & derivatives*
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Pargyline / chemistry
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Propylamines / chemistry*
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Stereoisomerism
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Thiones / chemical synthesis*
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Transition Elements / chemistry*
Substances
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Imidazoles
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Propylamines
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Thiones
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Transition Elements
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propargylamine
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Ethylenethiourea
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Gold
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imidazole
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Pargyline