Borohydride reduction of pyridinium salts. V. Thermal dimerization of 1,6-dihydro-1-methylpyridine-2-carbonitrile.
- Liberatore F.
- Casini A
- Carelli V
- Arnone A
- Mondelli R
DOIAbstract
The 1,6-dihydropyridine I, obtained by NaBH4 redn. of 2-cyano-1-methylpyridinium iodide, undergoes a thermal dimerization to give the cyclobutane deriv. II. II rearranges, by heating, to the isomeric ethenonaphthyridine III (R = H). Label scrambling observed at 110 in III (R = H) reveals a degenerate thermal [3.3] sigmatropic shift
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