Novel synthesis of 2-naphthol Mannich bases and their NMR behaviour

Jha, Amitabh; Paul, Nawal K.; Trikha, Smriti; Cameron, T. Stanley
June 2006
Canadian Journal of Chemistry;Jun2006, Vol. 84 Issue 6, p843
Academic Journal
A novel two-step procedure involving the formation of 1-arylidene-2-tetralones from 2-tetralone and subsequent Michael addition of a cyclic secondary amine on the alkenone followed by in situ aerial oxidation was developed to produce 2-naphthol Mannich bases. A simple microwave-assisted one-pot synthesis of 2-naphthol Mannich bases was also carried out under solvent-free conditions from 2-naphthol and corresponding aldehydes and amines in the presence of p-toluenesulfonic acid. The compounds of this series displayed interesting NMR behaviour. Extensive variable-temperature NMR investigations, including HSQC experiments, are herein reported. NMR results on the conformation in solution phase were found to be consistent with the X-ray crystal structure in the solid state.


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