Synthesis 2017; 49(11): 2575-2583
DOI: 10.1055/s-0036-1588955
paper
© Georg Thieme Verlag Stuttgart · New York

Pd-Catalyzed Efficient Synthesis of Azacoumestans Via Intramolecular Cross Coupling of 4-(Arylamino)coumarins in the Presence of Copper Acetate under Microwaves[1]

Thomas Balalas
a   Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece   Email: klitinas@chem.auth.gr
,
Alaa Abdul-Sada
b   Sussex University, School of Life Science, Chemistry Department, Falmer, Brighton, BN1 9QJ, UK
,
Dimitra J. Hadjipavlou-Litina
c   Department of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece
,
Konstantinos E. Litinas*
a   Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece   Email: klitinas@chem.auth.gr
› Author Affiliations
Further Information

Publication History

Received: 16 December 2016

Accepted after revision: 27 January 2017

Publication Date:
22 February 2017 (online)


Abstract

Azacoumestans have been synthesized in excellent yields by the Pd-catalyzed oxidative coupling of 4-(arylamino)coumarins in the presence of Cu(OAc)2 in acetic acid under microwave irradiation. 4-(Arylamino)coumarins, even those substituted with an electron-withdrawing group, have been prepared almost quantitatively by the reaction of arylamines with 4-bromocoumarin under microwave irradiation in water or by Pd-catalyzed C–N coupling under heating. Preliminary biological tests indicated significant inhibition of soybean lipoxygenase and antilipid peroxidation.

Supporting Information

 
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