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Synthesis of functionalized imidazolidine-2-thiones via NHC/base-promoted aza-benzoin/aza-acetalization domino reactions

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Abstract

A strategy for the synthesis of biologically relevant 5-hydroxy-imidazolidine-2-thione derivatives is presented. A novel class of α-sulfonylamines have been suitably prepared (46–81% yield) as precursors of formal benzylidenethiourea acceptors; these are generated in situ and intercepted by N-heterocyclic carbene (NHC)-activated aldehydes affording open-chain aza-benzoin-type adducts, which in turn undergo an intramolecular aza-acetalization reaction in a one-pot fashion. A thiazolium salt/triethylamine couple proved to be the more effective system to trigger the domino sequence giving the target heterocycles in good yields (45–97%) and diastereoselectivities (up to 99 : 1 dr). The multigram scale synthesis and elaboration of a selected 5-hydroxy-imidazolidine-2-thione compound is also described.

Graphical abstract: Synthesis of functionalized imidazolidine-2-thiones via NHC/base-promoted aza-benzoin/aza-acetalization domino reactions

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Publication details

The article was received on 08 Sep 2017, accepted on 03 Oct 2017 and first published on 03 Oct 2017


Article type: Paper
DOI: 10.1039/C7OB02259J
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Synthesis of functionalized imidazolidine-2-thiones via NHC/base-promoted aza-benzoin/aza-acetalization domino reactions

    G. Di Carmine, D. Ragno, C. De Risi, O. Bortolini, P. P. Giovannini, G. Fantin and A. Massi, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB02259J

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