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The chemistry of coumarin derivatives part 2. reaction of 4 hydroxycoumarin with alpha beta unsaturated aldehydes

The chemistry of coumarin derivatives part 2. reaction of 4 hydroxycoumarin with alpha beta unsaturated aldehydes

Helvetica Chimica Acta 73(7): 1865-1878

ISSN/ISBN: 0018-019X

DOI: 10.1002/hlca.19900730709

4-Hydroxycoumarin (=4-hydroxy-2H-1-benzopyran-2-one) reacts with enals to give 1,2- or 1,4-addition products, depending on the nature and relative location of the substituents of the olefinic double bond (Scheme 2). The resulting adducts further react intra- or intermolecularly affording dimeric coumarins or pyranocoumarins in the case of 1,2-addition and acetalic pyranocoumarins in the case of 1,4-addition. With enals bearing alkyl groups at C(.beta.), 2H-pyrano[3,2-c)coumarins are the only products formed, and the reaction represent an easy and straightforward entry into this class of recently described biologically active natural products.

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Accession: 007877291

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