The redeeming features of reaction of the 8-formyl-7-hydroxychromones with malononitrile

Oleg Lozinski; Tatyana Shokol; Oleg Shishkin; Vladimir Medvediev; Vladimir Khilya

doi:10.17721/fujcV2I1P10-15

Authors

Oleg Lozinski Department of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska Street, 64/13, Kyiv 01601, Ukraine
Tatyana Shokol Department of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska Street, 64/13, Kyiv 01601, Ukraine
Oleg Shishkin Division of Functional Materials Chemistry, SSI ”Institute for Single Crystals” of National Academy of Science of Ukraine, 60 Lenina ave., Kharkiv, 61001, Ukraine Department of Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody sq., Kharkiv, 61122, Ukraine
Vladimir Medvediev Division of Functional Materials Chemistry, SSI ”Institute for Single Crystals” of National Academy of Science of Ukraine, 60 Lenina ave., Kharkiv, 61001, Ukraine
Vladimir Khilya Department of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska Street, 64/13, Kyiv 01601, Ukraine

DOI:

https://doi.org/10.17721/fujcV2I1P10-15

Keywords:

malononitrile, 8-formyl-7-hydroxychromone, Knoevenagel reaction, Michael addition

Abstract

A range of 4H,8H-pyrano[2,3-f]chromen-4,8-diones have been prepared using Knoevenagel reaction of the 8-formyl-7-hydroxychromones with malononitrile. The 4H,8H-pyrano[2,3-f]chromen-4,8-dione derivative was also obtained through the acid hydrolysis of the 8-imino-4H,8H-pyrano[2,3-f]chromen-4-one. 8-Formyl-7-hydroxychromone 1 was found to add two molecules of malononitrile through Michael addition resulting in formation of the 2-[8-amino-3-(4-chlorophenyl)-9-cyano-2-methyl-4-oxo-4H,10H-pyrano[2,3-f]chromen-10-yl]malononitrile.

Supplementary information (CIF file)

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