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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 *
Faculty of Pharmacy, Medical University of Sofia, Dunav 2, BG-1000 Sofia, Bulgaria
* Author to whom correspondence should be addressed.
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 (CC BY 3.0).
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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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