E. Biehl, U. N. Rao
2002
Citations
0
Influential Citations
5
Citations
Journal
Heterocycles
Abstract
2-Methyl- and 3-ethyl-3H-pyrrolo[2,3-c]isoquinolines and 2-methyl-3H-pyrrolo[2,3-c][1,7]naphthyridines possessing a C-5 saturated heterocyclic ring were prepared from corresponding 4-alkenyl-3-amino-isoquinoline or naphthyridinevia palladium-assisted cyclization under catalytic conditions. Similar treatment of 3-prenyl derivatives of isoquinolines and naphthyridines possessing 6- alkyl groups gave 3,3,-dimethyl-3,4-dihydrobenzo[c]- and 3,4-dihydropyridino[4,3-c]naphthyridines, respectively. The Hegedus precursors were synthesized by alkenylation of 2-cyanomethylbenzonitrile or 3-cyanomethylpyridine-2-carbonitrile followed by base-mediated cyclization of α-alkenyl derivatives so formed using lithium amides or alkyllithiums.