Synthesis of α-Nitro Carbonyls via Nitrations in Flow.
Reported is a safe, rapid method for the synthesis of α-nitro esters via the trapping of nitronium ions. The two-stage nitration and subsequent deacetylation of readily available 1,3-dicarbonyl compounds was achieved using a biphasic semicontinuous approach. α-Nitro esters and amides were obtained in good overall yields (53-84%). Some of the α-nitro-1,3-dicarbonyl intermediates exhibit enhanced reactivity and undergo an acid-catalyzed Nef-type reaction to α-oxo-carbonyls.
Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.
Anna
A
Chentsova
Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.
Dmitry B
DB
Ushakov
Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.|Institute of Chemistry and Biochemistry, Freie Universität Berlin , Arnimallee 22, 14195 Berlin, Germany.
Peter H
PH
Seeberger
Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.
Kerry
K
Gilmore