1044258-40-3Relevant academic research and scientific papers
Scaffold preparation and parallel synthesis of arrays of 5,6,7,8-tetrahydropyrrolo-azepinones in the solution phase
Piras, Leonarda,Genesio, Eva,Ghiron, Chiara,Taddei, Maurizio
, p. 2789 - 2800 (2008)
An efficient synthesis of a pyrrolo-azepine scaffold for the parallel preparation of an array of (oxo-pyrrolo-azepinyl)-acetamides is described. The Stetter cyclisation of 1,3-cyclohexanedione with ethyl bromopyruvate was the key reaction in the assembly of a tetrahydrobenzofuran substrate which was submitted to a rapid transformation into a tetrahydroindole by microwave-assisted cyclocondensation in the presence of glycine. The carbonyl group was then stereoselectively transformed into the corresponding (Z)-oxime which gave the pyrrolo-azepinone by Beckmann rearrangement in the presence of polyphosphoric acid. Trimethylaluminiummediated amidation gave the corresponding amides which were finally N-alkylated at the 5-position to give 52 diverse (pyrrolo-azepinyl)acetamides, showing an appreciable exploration of the chemical space around the central heterocyclic core. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
