Synthesis of new heterocyclic analogs of linezolid

Article abstract of DOI:10.1016/j.tetlet.2015.09.065

We have previously attempted to prepare 5-(4-morpholinyl)-2-aminothiophene (3) by reducing 5-(4-morpholinyl)-2-nitrothiophene (2), to prepare a precursor for the preparation of thienyloxazolidinones as potential linezolid-like antibiotics. This strategy failed, but allowed us to define an interesting reductive aromatization reaction. We have now succeeded in producing thienyloxazolidinones using an alternative strategy, initiating from 5-(4-morpholinyl)thiophene-2-carboxaldehyde (8). This Letter describes the synthesis of thienyloxazolidinone 14, which is a key intermediate for the preparation of new oxazolidinone antibiotics with a thiophene core.