Heterocyclic Ortho-Aminocarbonyl Compounds in the Friedländer Reaction Promoted by Chlorotrimethylsilane

A possibility of introduction of heterocyclic ortho-aminoketones into promoted by TMSCI Friedländer reaction with a wide set of α-methylenecarbonyl compounds was studied. A convenient synthetical method to obtain heterofused pyridine systems was elaborated: its scope and limitations were established as well. A set of derivatives of thieno[2,3-b]pyridines, [1]benzofuro[3,2-b]pyridines, 5H-chromeno[2,3-b]pyridin-5-ones, pyrido[2,3-d]pyrimidin-2,4(1H,3H)-diones was obtained in high preparative yields.

Ryabukhin S. V.; Plaskon A. S.; Naumchik V. S.; Volochnyuk D. M.; Pipko S. E.; Tolmachev A. A.
Heterocycles 2007, 71 (11), 2397-2411
DOI: 10.3987/COM-07-11128