Bicyclic unsaturated structures containing one or more nitrogen atom appear in a wide range of organic compounds. In particular, the [b]-fused pyridine is a frequent structural motif, with striking biological activities. However, there is still a lack for general methods, with respect to the reaction conditions or the scope. In order to over-ride these limitations, a new synthetic procedure for preparation of the pyridine ring starting from β–aminoacrylonitrile is proposed using a procedure relying on a trichloromethyl-activated alkene. The reactivity of pyrazolo[3,4-b]pyridine, a subclass of [b]-fused pyridine, has been also investigated. Some late-stage functionnalization have been developped, relying on palladium-catalyzed chemistry. Three positions of the pyrazolopyridine core have been arylated, thus giving access to new structures.

Synthesis and functionalization of [b]-fused pyridine compounds

2019 Fall National Meeting

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