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Issue 5, 2018
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One-pot cascade synthesis of azabicycles via the nitro-Mannich reaction and N-alkylation

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Abstract

A one-pot, metal-free process for the synthesis of azabicycles is developed. The key transformations involved a cascade of double intramolecular cyclizations via the nitro-Mannich reaction and N-alkylation, providing various ring systems of azabicycles in yields up to 81% and an isomeric ratio of 62 : 1. This approach offers considerable advantages in terms of the handling of small molecules, the flexibility to introduce a functionalized side chain, and gives direct access to various azabicycles.

Graphical abstract: One-pot cascade synthesis of azabicycles via the nitro-Mannich reaction and N-alkylation

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Publication details

The article was received on 14 Dec 2017, accepted on 08 Jan 2018 and first published on 08 Jan 2018


Article type: Communication
DOI: 10.1039/C7OB03104A
Citation: Org. Biomol. Chem., 2018,16, 707-711
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    One-pot cascade synthesis of azabicycles via the nitro-Mannich reaction and N-alkylation

    W. Disadee and S. Ruchirawat, Org. Biomol. Chem., 2018, 16, 707
    DOI: 10.1039/C7OB03104A

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