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Issue 3, 2018
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Synthesis of thiazolidine-thiones, imino-thiazolidines and oxazolidines via the base promoted cyclisation of epoxy-sulfonamides and heterocumulenes

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Abstract

Epoxy-sulfonamides react with heterocumulenes (carbon disulfide/isothiocyanates/isocyanates) in the presence of a base to afford ring expansion products in good to high yields with excellent regioselectivity. N-(2-Bromoethyl)-sulfonamides can also be employed as substrates. This reaction proceeds through a 5-exo-tet pathway without forming aziridine intermediates.

Graphical abstract: Synthesis of thiazolidine-thiones, imino-thiazolidines and oxazolidines via the base promoted cyclisation of epoxy-sulfonamides and heterocumulenes

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Publication details

The article was received on 25 Nov 2017, accepted on 05 Dec 2017 and first published on 06 Dec 2017


Article type: Paper
DOI: 10.1039/C7OB02915B
Citation: Org. Biomol. Chem., 2018,16, 402-413
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    Synthesis of thiazolidine-thiones, imino-thiazolidines and oxazolidines via the base promoted cyclisation of epoxy-sulfonamides and heterocumulenes

    M. Anitha and K. C. K. Swamy, Org. Biomol. Chem., 2018, 16, 402
    DOI: 10.1039/C7OB02915B

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