One-Pot, Three-Component Uncatalyzed Quantitative Synthesis of New Aminonaphthols (Betti Bases) in Water

Abstract

One-pot, three-component reaction of 2-naphthol, aromatic aldehyde, and heteroaryl amine in water at room temperature leads to the formation of the corresponding aminonaphthols (Betti bases). Reaction details and study of enantiomeric resolution of 1-(p-methylphenyl (2-pyrazinylamino) methyl) naphthalene-2-ol with the aid of ¹H NMR spectroscopy using chiral europium shift reagent is presented.

Keywords:

• Aminonaphthol
• Betti base
• 2-naphthol
• shift reagent

ACKNOWLEDGMENT

The authors thank the Research Council of the University of Tehran and Payame Noor University of Qazvin for financial support.

Notes

^a In the presence of formic acid as catalyst.

^b Reaction times of 24 to 48 h were needed for reactions to be completed at room temperature.

^c Reaction times of 5 to 15 min were needed for comparable yields under reflux conditions.