Convenient synthesis and unusual reactivity of 2-oxo-2H,5H-pyrano[3,2-c]chromenes |
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Authors: | Margita Lácová Andrej Bohá? |
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Institution: | a Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, SK-842 15 Bratislava, Slovak Republic b Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, SK-842 15 Bratislava, Slovak Republic |
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Abstract: | The reaction of 4-oxo-4H-chromen-3-carbaldehydes with coumarin-4-acetic acids under the Perkin conditions follows an interesting pathway that involves aldol reaction and subsequent intramolecular lactonization to afford 2-oxo-2H,5H-pyrano3,2-c]chromene skeleton. In contrast to chromone-3-carbaldehydes, the same reaction with chromone-2-carbaldehydes yielded only the aldol condensation product. The reaction was performed under thermal and microwave conditions. The reactivity of 2-oxo-2H,5H-pyrano3,2-c]chromenes in water, alcohol and acetic acid was described. |
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Keywords: | Chromenes Rearrangement Condensation Microwave |
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