Synthesis of Benzo[c][2,7]Naphthyridines by One-Pot Multicomponent Reaction Using Ceric(IV) Ammonium Nitrate

Abstract

A new, one-pot, three-component reaction for the synthesis of benzo[c][2,7]naphthyridines has been achieved from aromatic amines, aromatic aldehydes, and N-carbethoxy-4-piperidone in the presence of a catalytic amount of ceric ammonium nitrate in good yields at room temperature. The advantages of this procedure are mild reaction conditions, low toxicity, and the use of inexpensive reagents. Apart from milder and environmentally benign conditions, this method involves a simple, reliable approach to give good yields of the desired products and is compatible with a wide range of functional groups.

GRAPHICAL ABSTRACT

Keywords:

• Ceric ammonium nitrate
• multicomponent reaction
• naphthyridines
• one-pot synthesis

Notes

^a Reaction conditions: The reaction was performed with aniline (1 mmol), benzaldehyde (1 mmol), N-carbethoxy-4-piperidone (1 mmol), and catalyst (10 mol%) in acetonitrile (5 mL) at room temperature.

^b Isolated yields after column chromatography.

^a Reaction conditions: The reaction was performed with aniline (1 mmol), benzaldehyde (1 mmol), N-carbethoxy-4-piperidone (1 mmol), and CAN in the given solvent (5 mL) at room temperature for 5 h.

^b Isolated yields after column chromatography.

^a Reaction conditions: The reaction was performed with anilines (1 mmol), aromatic aldehydes (1 mmol), N-carbethoxy-4-piperidone (1 mmol), and 10 mol% of CAN in acetonitrile (5 mL) at room temperature.

^b Isolated yields after column chromatography.