From thienodiazepinediones to thienopyridinones: flexible synthesis of substituted thieno[3,2-e][1,4]diazepinones and 6-aminothieno[3,2-b]pyridinones.
N-Substituted thienodiazepinedione opening with a series of organomagnesium bromides allowed the subsequent cyclization to the seven-membered ring thieno[3,2-e][1,4]diazepinone in 52-99% yields or to the six-membered ring thieno[3,2-b]pyridinones in 45-55% yields. Effective syntheses introducing considerable diversity onto these valuable scaffolds are described.
Brouillette
Yann
Y
Institut des Biomolécules Max-Mousseron, UMR 5247, CNRS, Universités Montpellier I et II, UFR desSciences Pharmaceutiques et Biologiques, 15 Avenue Charles Flahault,34093 Montpellier Cedex 5, France.
Martinez
Jean
J
Lisowski
Vincent
V
D000586:Amination; D001372:Aza Compounds / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D011728:Pyridones / Q000737:chemistry*
D001372:Aza Compounds; D009942:Organometallic Compounds; D011728:Pyridones; D009584:Nitrogen