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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 45, 2015 - Issue 12
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Original Articles

Molecular Diversity from the L-Proline-Catalyzed, Three-Component Reactions of 4-Hydroxycoumarin, Aldehyde, and 3-Aminopyrazole or 1,3-Dimethyl-6-aminouracil

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Pages 1442-1450 | Received 20 Nov 2014, Published online: 15 Apr 2015
 

Abstract

The three-component reaction of 4-hydroxycoumarin, aldehyde, and aminopyrazole in the presence of a catalytic amount of L-proline in ethanol under reflux conditions provided the cyclized product (dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridine-6(7H)-one), whereas under similar reaction conditions, replacing aminopyrazole by 1,3-dimethyl-6-aminouracil provided the acyclic three-component product (6-amino-5-((4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione). This method is metal free and atom economical, and avoids column chromatographic purification as all the products can be purified by recrystallization.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

The authors are grateful to IIT Patna and SAIF Panjab University for providing analytical facilities for characterization of compounds, and to SAIF-IIT Madras for providing single-crystal x-ray crystallographic data.

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