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Base-Mediated Hydroamination of Propargylamine: A Regioselective Intramolecular 5-exo-dig Cycloisomerization en Route to Imidazole-2-thione

Alok Ranjan, Ragini Yerande, Prasad B. Wakchaure, Swapnil G. Yerande* and Dattatraya H. Dethe*

*Acoris Research, 3A International Biotech Park, Hinjewadi, Pune 411057, Maharashtra; Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India, Email: swapnilyerandegmail.com, ddetheiitk.ac.in

A. Ranjan, R. Yerande, P. B. Wakchaure, S. G Yerande, D. H. Dethe, Org. Lett., 2014, 16, 5788-5791.

DOI: 10.1021/ol502871r (free Supporting Information)


Abstract

An intramolecular transition-metal-free base-mediated hydroamination of propargylamine with isothiocyanates enables an atom-economical, regioselective synthesis of diversely substituted imidazole-2-thiones and spiro-cyclic imidazolidine-2-thiones in good yields via  intramolecular 5-exo-dig cycloisomerization.

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Key Words

Imidazolones, N-Heterocycles


ID: J54-Y2014