Abstract
Ethylenediamine-derived β-enamino amides are used as equivalents of amide enolate synthons in C-acylation reactions with N-protected amino acids. Domino fragmentation of the obtained intermediates leads to functionalised β-keto amides, bearing a protected amino group in their side chain.
Highlights
The acylation of amide enolates is one of the main synthetic approaches towards β-keto amides and has found numerous applications [1,2,3,4,5,6,7,8,9]
With regard to acylation reactions, maybe most important among these are some nitriles, which can be successfully acylated at the alpha position [13,14,15] and hydrated [13,16,17,18,19,20] to reveal a primary amide functionality
A contribution of ours in this area is the application of ethylenediamine-derived β-enamino amides as synthetic equivalents of primary and secondary amide enolate synthons in reactions with acid chlorides [22]
Summary
The acylation of amide enolates is one of the main synthetic approaches towards β-keto amides and has found numerous applications [1,2,3,4,5,6,7,8,9]. To extend the scope of the methodology, we have explored the acylation of these reagents with suitably activated amino acids, in order to prepare functionalised β-keto amides, bearing a protected amino group in their side chain. Keto amides of this type are excellent precursors to various heterocyclic systems and are interesting as building blocks for many biologically active substances [5,6,7,8,9,11,23,24,25,26,27,28,29,30,31,32,33]
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