Abstract
Treatment of 2-picoline with BunLi in THF affords its corresponding 2-picolyl lithium salt in a high yield. The insertion of benzonitrile into the LiC bond of 2-picolyl lithium followed by acidic hydrolysis yields the corresponding β-pyridyl ketone (1), and diketone compounds (2) is obtained from 1 by intermolecular elimination of proton under the base condition. Similarly, the insertion of terephthalonitrile into 2-picolyl lithium leads to a 1,4-phenyl-linked pyridyl-azaalyl dilithium complex 4, followed by acidic hydrolysis yields corresponding 1,4-phenyl-linked dipyridylketone 3. The probable reaction pathway for the formation of 2 has been investigated. Compound 2 and 4 have been characterized by single-crystal X-ray crystallography.
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