A. Deshmukh, E. Biehl
1992
Citations
0
Influential Citations
6
Citations
Journal
Heterocycles
Abstract
The synthesis of 1-amino-3,8-dipyridylmethyl-7-methylisoquinoline (3) accomplished by the reaction of 2-chloro-1,4-dimethylbenzene with pyridylacetonitrile under aryne forming conditions is reported. A mechanism is suggested in which a cyano group is inroduced ortho to one of the ring methyl groups via tandem-addition rearrangement aryne process. Such positioning of the cyano group facilitates lithiation of the adjacent methyl group by stabilizing the resulting CH 2 Li group by resonance delocalization. The CH 2 Li group then reacts with another molecule of pyridylacetonitrile affording a cyano-imine intermediate which condenses intramolecularly to afford 3 after a successive tautomeric shift and proton quench