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Molecules 2004, 9(8), 627-631; doi:10.3390/90800627
Article

Convenient Replacement of the Hydroxy by an Amino Group in 4 Hydroxycoumarin and 4-Hydroxy-6-methyl-2-pyrone under Microwave Irradiation

 and *
Received: 4 June 2004 / Accepted: 18 June 2004 / Published: 31 July 2004
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Abstract

The reaction of 4-hydroxycoumarin (1) with some primary amines 2a-h and morpholine (2i) under microwave irradiation occurred without opening of the lactone ring to give N-substituted 4-aminocoumarins 3a-i in excellent yields. Under the same experimental conditions, 4-hydroxy-6-methyl-2-pyrone (4) reacted with benzylamine (2e) or 2-phenyl- ethylamine (2f) to give the corresponding N,N'-disubstituted 4-amino-6-methyl-2-pyridones 5e,f. The main advantages of this procedure are dramatically shortened reaction times, higher amine utilization and considerably improved yields.
Keywords: 4-Hydroxycoumarin; 4-aminocoumarins; 4-hydroxy-2-pyrones; 4-amino-2-pyri- dones; microwave irradiation; nucleophilic replacement. 4-Hydroxycoumarin; 4-aminocoumarins; 4-hydroxy-2-pyrones; 4-amino-2-pyri- dones; microwave irradiation; nucleophilic replacement.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Stoyanov, E.V.; Ivanov, I.C. Convenient Replacement of the Hydroxy by an Amino Group in 4 Hydroxycoumarin and 4-Hydroxy-6-methyl-2-pyrone under Microwave Irradiation. Molecules 2004, 9, 627-631.

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