The preparation of phenyl pyridyl ketones by the action of 2‐lithiopyridine or 3‐lithiopyridine on benzoic anhydride, ethyl benzoate or benzonitrile is described: di‐pyridyl‐phenyl‐carbinols are produced by the further action of lithiopyridine on the ketones so obtained.The action of 2‐lithiopyridine on 2‐cyanopyridine or ethyl picolinate gives bis‐(pyridyl‐2) ketone; in a similar way bis‐(pyridyl‐3) ketone is prepared and some other di‐pyridyl ketones.By the action of 2‐lithiopyridine on bis‐(pyridyl‐2) ketone there is obtained tris‐(pyridyl‐2)‐carbinol; tris‐(pyridyl‐3)‐carbinol has been synthesised in a similar way.
94th Communication on pyridine derivatives. In communication I11 of this series we described the preparation of a few 3-pyridyl-carbinols and of a pyridine derivative with an unsaturated side chain, 2-methyl-3-(pyridyl-3) -propene-1, by the application of the Grignard reaction to 3-bromopyridine 2 ) . In the present communication, further applications of this synthetic method are described. W e have again applied Grignard's so-called ,,methode de I'entrainement", namely by causing a mixture of 3-bromopyridine and ethyl bromide to react on magnesium. W e are not going into the mechanism of the formation of the pyridyl magnesium compound, since our research about this is not yet completed, and are confining ourselves to the description of the method of preparation. Through an improvement of the process formerly used (see the experimental part) we have obtained satisfactory yields in a number of cases.In the formulae below, the pyridyl magnesium compound is designated diagrammatically by I. This formulation is a simplification, since we may have to do with a complex compound in which I is present in some form or other and which reacts with the second component as a 3-pyridylmagnesium bromide. ,The following is a summary of the syntheses that have been carried out.
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