APPLICATIONS OF ORGANO-LITHIUM AND RELATED REAGENTS IN SYNTHESIS .3. A GENERAL STUDY OF THE REACTION OF LITHIUM ALKYLS WITH PYRIDINE KETONES

The reaction of MeLi [methyl lithium] and PhLi [phenyl lithium] with acetylpyridines (1a-c) and their annelated derivatives (2a), (2b), (3) and (4) was examined. The 3- and 4-pyridyl ketones (1b), (1c), (3) and (4) gave similar results to acetophenone and 3,4-dihydronaphthalen-1 (2H)-one. In the case of the 2-pyridyl ketone (1a), (2a) and (2b) unexpectedly low yields of products resulted from the addition of RLi to the carbonyl group; the reaction was efficiently enhanced by initially adding on additional amount of LiBr. These results were counted for by the relation of RLi or LiBr by the 2-pyridyl ketones [These compounds have potential antiulcer and antisecretory activity].