One-pot cascade synthesis of azabicycles via the nitro-Mannich reaction and N-alkylation.

Org Biomol Chem

Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Laksi, Bangkok 10210, Thailand.

Published: January 2018

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Article 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.

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http://dx.doi.org/10.1039/c7ob03104aDOI Listing

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