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  • Title: Base-mediated hydroamination of propargylamine: a regioselective intramolecular 5-exo-dig cycloisomerization en route to imidazole-2-thione.
    Author: Ranjan A, Yerande R, Wakchaure PB, Yerande SG, Dethe DH.
    Journal: Org Lett; 2014 Nov 07; 16(21):5788-91. PubMed ID: 25351666.
    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.
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