Novel synthesis of 2-naphthol Mannich bases and their NMR behaviour
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 synt...
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| Veröffentlicht in: | Canadian journal of chemistry 2006-06, Vol.84 (6), p.843-853 |
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| container_title | Canadian journal of chemistry |
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| creator | Jha, Amitabh Paul, Nawal K Trikha, Smriti Cameron, T Stanley |
| description | 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.Key words: Mannich bases, microwave-assisted Mannich reaction, temperature-variable NMR spectroscopy, NMR dynamics, X-ray crystallography. |
| doi_str_mv | 10.1139/v06-081 |
| format | Article |
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| subjects | Aldehydes Amines Analysis Chemical synthesis NMR Nuclear magnetic resonance Spectrum analysis Studies Temperature X-ray crystallography |
| title | Novel synthesis of 2-naphthol Mannich bases and their NMR behaviour |
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