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Issue 8, 2018
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5-Methylene N-acyl dihydropyridazinium ions as novel Mannich-type acceptors in 1,4 additions of nucleophiles

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Abstract

1,4,5,6-Tetrahydropyridazine featuring an iminium cation flanked by an exocyclic double bond was successfully employed as an N-acyliminium acceptor. Thus, in the presence of a Lewis acid (BF3·OEt2), generation and in situ interception of 5-methylene N-acyl dihydropyridazinium species with a range of various nucleophiles afforded diversified and functionalized 5-methylenyl-1,4-dihydropyridazine derivatives in good yields with excellent γ′-regioselectivity.

Graphical abstract: 5-Methylene N-acyl dihydropyridazinium ions as novel Mannich-type acceptors in 1,4 additions of nucleophiles

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Publication details

The article was received on 11 Jan 2018, accepted on 19 Feb 2018 and first published on 19 Feb 2018


Article type: Research Article
DOI: 10.1039/C8QO00032H
Citation: Org. Chem. Front., 2018,5, 1308-1311
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    5-Methylene N-acyl dihydropyridazinium ions as novel Mannich-type acceptors in 1,4 additions of nucleophiles

    G. Mari, L. De Crescentini, F. Mantellini, S. Santeusanio and G. Favi, Org. Chem. Front., 2018, 5, 1308
    DOI: 10.1039/C8QO00032H

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