Abstract
A one-pot, three-component reaction of 4-hydroxyquinolin-2(1H)-one, malononitrile, and various aldehydes for the synthesis of 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c]quinolin-5-one derivatives is reported. The reaction is performed without any catalysts in a mixed solvent of water and ethanol to give products in good yields. The present method provided a clean, simple, and economical alternative for the synthesis of potential biologically active pyranoquinoline derivatives.
Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.
GRAPHICAL ABSTRACT
![](/cms/asset/927a7367-5024-485d-8969-9ba643bd3445/lsyc_a_686647_o_uf0001.gif)
ACKNOWLEDGMENT
Financial support from the Natural Science Foundation Project of CQ CSTC (2009A5051) is gratefully acknowledged.
Notes
a Reaction conditions: 4-hydroxyquinolin-2(1H)-one 1 (1.0 mmol), benzaldehyde 2j (1.2 mmol), and malononitrile 3 (1.2 mmol) in solvent (2 ml) at the reflux temperature.
b Isolated yields.
a Reaction conditions: 4-hydroxyquinolin-2(1H)-one 1 (1.0 mmol), aldehyde 2 (1.2 mmol), and malononitrile 3 (1.2 mmol) in H2O–EtOH (1:1) (2 mL) under reflux.
b Isolated yields.