Simple, Catalyst-Free, One-Pot Procedure for the Synthesis of 2-Amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c]quinolin-5-one Derivatives

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.

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GRAPHICAL ABSTRACT

Keywords:

• Catalyst-free
• multicomponent reaction
• pyranoquinoline derivative
• synthesis

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.