Microwave-Assisted Synthesis of Novel (5-Nitropyridin-2-yl)alkyl and (5-Nitropyridin-3-yl)alkyl Carbamates

A straightforward approach to novel (5-nitropyridin-2-yl)alkyl and (5-nitropyridin-3-yl)alkyl carbamate building blocks is presented in this study. Their construction is achieved by condensation of N-carbamate α- and β-amino carbonyl derivatives with 1-methyl-3,5-dinitro-2-pyridone 1 under microwave...

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Veröffentlicht in:Journal of organic chemistry 2009-03, Vol.74 (5), p.1932-1938
Hauptverfasser: Henry, Christophe, Haupt, Andreas, Turner, Sean C
Format: Artikel
Sprache:eng
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Zusammenfassung:A straightforward approach to novel (5-nitropyridin-2-yl)alkyl and (5-nitropyridin-3-yl)alkyl carbamate building blocks is presented in this study. Their construction is achieved by condensation of N-carbamate α- and β-amino carbonyl derivatives with 1-methyl-3,5-dinitro-2-pyridone 1 under microwave irradiation. Judiciously chosen modifications in the nature of the parent carbonyl starting material has influenced the regiochemical outcome of the reaction and allowed an efficient access to novel nitrogen-containing scaffolds. Compounds sharing morphological similarities have been gathered in three libraries differing from each other in a single structural parameter.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo802439d