Chlorotrimethylsilane-Mediated Synthesis of Functionalized Fused Pyridines: Reaction of 3-Formylchromones with Electron-Rich Aminoheterocycles

Sergey V. Ryabukhin; Andrey S. Plaskon; Dmitriy M. Volochnyuk; Andrey A. Tolmachev

doi:10.1055/s-2007-983704

PAPER

Chlorotrimethylsilane-Mediated Synthesis of Functionalized Fused Pyridines: Reaction of 3-Formylchromones with Electron-Rich Aminoheterocycles

Sergey V. Ryabukhin^a,b, Andrey S. Plaskon^a,b, Dmitriy M. Volochnyuk*^a,c, Andrey A. Tolmachev^b
^a Enamine Ltd., Alexandra Matrosova st. 23, 01103 Kiev, Ukraine
^b National Taras Shevchenko University of Kiev, Volodimirska st. 62, 01033 Kiev, Ukraine
^c Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, Kiev-94, 02094, Ukraine
Fax: +380(44)5373253; e-Mail: D.Volochnyuk@enamine.net;

Abstract

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Abstract

The reaction of 3-formylchromones with aminoheterocycles was investigated. A simple and flexible general procedure for annulation of 5-(2-hydroxybenzoyl)pyridines was proposed. The best reaction conditions were found to be heating the reaction mixture in DMF in the presence of Me₃SiCl as a promoter and water as scavenger.

Key words

3-formylchromones - aminoheterocycles - anilines - fused pyridines - quinolines - cyclization - chlorotrimethylsilane

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References

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