Issue 24, 2012

The Rabe amination after a century: direct addition of N-heterocycles to carbonyl compounds

Abstract

A catalytic version of the Rabe electrophilic amination is presented. This kind of reaction was originally employed in 1918 in a key step for the conversion of quinotoxine to quinine. Ketones and α-substituted aldehydes give the corresponding α-aminated carbonyl compounds in moderate yield. α,α-Unsubstituted aldehydes give rise to amino ketones via a novel rearrangement.

Graphical abstract: The Rabe amination after a century: direct addition of N-heterocycles to carbonyl compounds

Supplementary files

Article information

Article type
Communication
Submitted
21 Mar 2012
Accepted
10 May 2012
First published
10 May 2012

Org. Biomol. Chem., 2012,10, 4692-4695

The Rabe amination after a century: direct addition of N-heterocycles to carbonyl compounds

D. M. Scarpino Schietroma, M. R. Monaco, V. Bucalossi, P. E. Walter, P. Gentili and M. Bella, Org. Biomol. Chem., 2012, 10, 4692 DOI: 10.1039/C2OB25595B

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