Letters in Organic Chemistry

Author(s): Vyacheslav Ya. Sosnovskikh and Roman A. Irgashev

DOI: 10.2174/157017807781212030

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Synthesis of 3-(Azolylmethylene)Chroman-4-ones via Addition of Indoles and N-Methylpyrrole to 3-(Polyfluoroacyl)Chromones

Page: [344 - 351] Pages: 8

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Abstract

Reactions of 3-(polyfluoroacyl)chromones with indole and N-methylindole in refluxing pyridine and Nmethylpyrrole under solvent-free conditions proceed at the C(2) atom of the chromone system with pyrone ring opening and subsequent cyclization to 2-hydroxy-3-(indol-3-ylmethylene- or pyrrol-2-ylmethylene)-2-(polyfluoroalkyl)chroman- 4-ones in good yields. Treatment of these compounds with morpholine gives trans-indolyl(pyrrolyl)chalcones.

Keywords: 3-(Polyfluoroacyl)chromones, indoles, N-methylpyrrole, 3-(azolylmethylene)chroman-4-ones, azolylchalcones