Aminomethylation of lithiated nicotinamide: access to new pyridolactams

Emilie Prieur (1) , Rabah Azzouz (1) , Geoffrey Deguest (1) , Corinne Fruit (1) , Laurent Bischoff (1) , Francis Marsais (2)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 IRCOF - Institut de Chimie Organique Fine

New 2,3-dihydropyrrolopyridinones were conveniently prepared by trapping lithiated pyridine carboxamides with highly reactive formimines. In this Letter, we report that a wide range of N-functionalised compounds can be synthesised in one step by this process, allowing the presence of ethers, acetals or ester moieties.

Keywords: Pyridine; Metalation; Formimine; Lactam; Aminomethylation

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry; Chemical Sciences; Medicinal Chemistry; Chemical Sciences; Radiochemistry; Chemical Sciences; Material chemistry; Chemical Sciences; Inorganic chemistry; Chemical Sciences; Catalysis

Emilie Prieur, Rabah Azzouz, Geoffrey Deguest, Corinne Fruit, Laurent Bischoff, et al.. Aminomethylation of lithiated nicotinamide: access to new pyridolactams. Tetrahedron Letters, 2008, 49 (3), pp.437-440. ⟨10.1016/j.tetlet.2007.11.109⟩. ⟨hal-02385012⟩