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Synthesis 2013; 45(10): 1380-1386
DOI: 10.1055/s-0032-1316908
DOI: 10.1055/s-0032-1316908
paper
Synthesis of Iminonitriles by Oxone/TBAB-Mediated One-Pot Oxidative Three-Component Strecker Reaction
Further Information
Publication History
Received: 18 March 2013
Accepted after revision: 20 March 2013
Publication Date:
08 April 2013 (online)
Abstract
Oxidative three-component reaction of aldehydes, amines, and TMSCN in a biphasic solvent system (toluene/H2O) containing Oxone, tetra-n-butylammonium bromide (TBAB) and sodium bicarbonate afforded α-iminonitriles in good to excellent yields. This oxidative Strecker reaction was applicable to a wide range of aldehydes and amines, aromatic or aliphatic, of different electronic and steric properties. Substituted 1-aza-2-cyano-1,3-dienes were also accessible using α,β-unsaturated aldehydes as inputs.
Key words
α-iminonitrile - Oxone - α-aminonitrile - oxidative three-component Strecker reaction - multicomponent reactionSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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Oxidative multicomponent reactions:
Oxidative multicomponent reactions incorporating an internal redox process, see: