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Di Carmine G, Ragno D, De Risi C, et al. Synthesis of functionalized imidazolidine-2-thiones via NHC/base-promoted aza-benzoin/aza-acetalization domino reactions. Org Biomol Chem. 2017;15(41):8788-8801doi: 10.1039/c7ob02259j.
Di Carmine, G., Ragno, D., De Risi, C., Bortolini, O., Giovannini, P. P., Fantin, G., & Massi, A. (2017). Synthesis of functionalized imidazolidine-2-thiones via NHC/base-promoted aza-benzoin/aza-acetalization domino reactions. Organic & biomolecular chemistry, 15(41), 8788-8801. https://doi.org/10.1039/c7ob02259j
Di Carmine, Graziano, et al. "Synthesis of functionalized imidazolidine-2-thiones via NHC/base-promoted aza-benzoin/aza-acetalization domino reactions." Organic & biomolecular chemistry vol. 15,41 (2017): 8788-8801. doi: https://doi.org/10.1039/c7ob02259j
Di Carmine G, Ragno D, De Risi C, Bortolini O, Giovannini PP, Fantin G, Massi A. Synthesis of functionalized imidazolidine-2-thiones via NHC/base-promoted aza-benzoin/aza-acetalization domino reactions. Org Biomol Chem. 2017 Oct 25;15(41):8788-8801. doi: 10.1039/c7ob02259j. PMID: 29019504.
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Org Biomol Chem. 2017 Oct 25;15(41):8788-8801. doi: 10.1039/c7ob02259j.

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

Organic & biomolecular chemistry

Graziano Di Carmine, Daniele Ragno, Carmela De Risi, Olga Bortolini, Pier Paolo Giovannini, Giancarlo Fantin, Alessandro Massi

Affiliations

  1. Dipartimento di Scienze Chimiche e Farmaceutiche, Università di Ferrara, Via Luigi Borsari, 46, I-44121 Ferrara, Italy. [email protected] [email protected].

PMID: 29019504 DOI: 10.1039/c7ob02259j

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.

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