Synthesis 2010(16): 2763-2766  
DOI: 10.1055/s-0029-1218835
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Synthesis of Bromo-Substituted 3-Arylcoumarins

Maria João Matos*a, Giovanna Delogub, Gianni Poddab, Lourdes Santanaa, Eugenio Uriartea
a Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Fax: +34(981)594912; e-Mail: mariacmatos@gmail.com;
b Dipartimento Farmaco Chimico Tecnologico, Università degli Studi di Cagliari, 09124 Cagliari, Italy
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Publikationsverlauf

Received 4 March 2010
Publikationsdatum:
25. Juni 2010 (online)

Abstract

Regioselective syntheses of 3-arylcoumarins possessing a bromine substituent either on the 3-aryl ring, the coumarin moiety or on a lateral chain of a coumarin is reported. The regioselectivity is influenced by the substituents present in the substrates. Two different bromination methods are described and compared. Perkin condensation of 5-methylsalicylaldehyde and phenylacetic acid or para-methoxyphenylacetic acid affords the desired coumarins. Three different bromine substitution patterns are accessed starting from 5-methylsalicylaldehyde.