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Paper | Regular issue | Vol 71, No. 11, 2007, pp.2397-2411
Published online, 25th July, 2007
DOI: 10.3987/COM-07-11128
Heterocyclic Ortho-Aminocarbonyl Compounds in the Friedländer Reaction Promoted by Chlorotrimethylsilane

Sergey V. Ryabukhin,* Andrey S. Plaskon, Vasiliy S. Naumchik, Dmitriy M. Volochnyuk, Sergey E. Pipko, and Andrey A. Tolmachev

*Enamine Ltd. 23 A. Matrosova St., 01103 Kyiv, Ukraine

Abstract

A possibility of introduction of heterocyclic ortho-aminoketones into promoted by TMSCl 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.