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

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Convenient replacement of the hydroxy by an amino group in 4 hydroxycoumarin and 4-hydroxy-6-methyl-2-pyrone under microwave irradiation.

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'-disubstit...

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Crystal structures of 4-methoxy-6-methyl- and 4-hydroxy-6-methyl-2-pyrones.

interesting results because of the regular arrangement of the molecules in the environment.1–3 We previously reported on the photocycloaddition reaction of 4-methoxy-6-methyl-2-pyrone (1a) (Fig. 1) with maleimide (2) in the solid state to give a highly stereoselective [2 + 2] cycloadduct4 owing to the formation of two sets of 1:1 complex crystals between (1a) and (2) (Fig. 1).5 The crystal show...

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Synthesis and Biological Evaluation of 4-hydroxychromenyl arylmethyl-6-hydroxy pyrimidine-2, 4-dione Derivatives

Background: An efficient, promoted tri-component catalytic reaction between barbituric acid (or N,N-dimethyl barbituric acid), 4-hydroxy coumarin, and a wide range of aryl aldehydes using zinc oxide nanowires (ZnO NWs) to obtain some new 4-hydroxychromenylarylmethyl-6-hydroxypyrimidine-2,4-diones is described. Method: The reactants were successfully condensed ...

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Biosynthesis of phlorisovalerophenone and 4-hydroxy-6-isobutyl-2-pyrone in Escherichia coli from glucose

BACKGROUND Type III polyketide synthases (PKSs) contribute to the synthesis of many economically important natural products, which are typically produced by direct extraction from plants or synthesized chemically. For example, humulone and lupulone (Fig. 1a) in hops (Humulus lupulus) account for the characteristic bitter taste of beer and display multiple pharmacological effects. 4-Hydroxy-6-me...

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A Facile Synthesis of 4-Hydroxycoumarin and 4-Hydroxy-2-quinolone Derivatives

Coumarin derivatives possessing diverse biological activities play important roles as versatile building blocks for the synthesis of natural products and biologically active compounds. In particular, 4-hydroxycoumarin derivatives, such as 4-hydroxycoumarin and 4-hydroxythiocoumarin, have been used as useful intermediates for the synthesis of anticoagulants, herbicides, and anticancer agents. Re...

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ژورنال

عنوان ژورنال: Molecules

سال: 2004

ISSN: 1420-3049

DOI: 10.3390/90800627