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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 23
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Original Articles

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

, &
Pages 4125-4138 | Received 18 May 2008, Published online: 31 Oct 2008
 

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.

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.

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