New α-Amido-α-aminonitrones
As Building Blocks for Constructing ­Heterocyclic Systems

Bartosz Trzewik; Dariusz Cież; Maciej Hodorowicz; Katarzyna Stadnicka

doi:10.1055/s-2008-1067236

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Synthesis 2008(18): 2977-2985
DOI: 10.1055/s-2008-1067236

PAPER

New α-Amido-α-aminonitrones As Building Blocks for Constructing Heterocyclic Systems

Bartosz Trzewik*, Dariusz Cież, Maciej Hodorowicz, Katarzyna Stadnicka
Faculty of Chemistry, Jagiellonian University, ul. Romana Ingardena 3, 30-060 Kraków, Poland
Fax: +48(12)6340515; e-Mail: trzewik@chemia.uj.edu.pl;

Further Information

Publication History

Received 27 May 2008
Publication Date:
22 August 2008 (online)

Abstract
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Abstract

New, stable α-amido-α-aminonitrones were obtained in good yields from 3-oxobutyric acid N-pyridin-2-ylamides and nitrosobenzene. The α-amido-α-aminonitrones were then used as new, versatile building blocks to obtaining various heterocycles with both bielectrophilic and binucleophilic reagents. With diiodomethane as reagent, 1,2,5-oxadiazine derivatives were formed, whereas reactions with aromatic 1,2-, 1,3- and 1,4-diamines yielded quinoxaline, quinazoline, perimidine, and dibenzo[d,f][1,3]diazepine derivatives, respectively.

Key words

building blocks - nitrones - heterocycles - alkylation - cyclisation

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